Diamond, Neil life and biography

Neil Leslie Diamond was born January 24, 1941, in Brooklyn, NY, the first of two sons born to Akeeba Diamond, who operated and owned a series of dry goods stores in the New York City borough, and Rose Diamond.
Diamond grew up in Brooklyn, albeit in changing locations as his father moved from store to store; he later claimed to have attended nine different schools and to have suffered socially as a result. He showed an early interest in music and took up singing and playing the guitar after seeing Pete Seeger perform at a camp he was attending as a teenager. In June 1958, he graduated from Abraham Lincoln High School, and that fall he enrolled at New York University, where he had won a fencing scholarship, as a premed student. But he seems to have spent much of his time writing songs and trying to place them at music publishing companies. He also formed a duo with Jack Packer, a friend of his younger brother's, and as Neil & Jack they signed a publishing contract with Allied Entertainment Corporation of America and a recording contract with its subsidiary, Duel Records. This resulted in the release of two singles, "You Are My Love"/"What Will I Do" in 1960 and "I'm Afraid"/"Till You've Tried Love" in 1961, Diamond's first commercially released recordings. (In 1996, he reissued "What Will I Do" on his box set In My Lifetime.) The discs were not successful, and Neil & Jack broke up when Packer enrolled at the Manhattan School of Music in January 1961. Diamond, meanwhile, had stopped attending NYU in 1960, but in 1961 he enrolled in the university's School of Commerce, where he maintained his student status until 1965.

On his own, Diamond continued trying to break into the music business as a songwriter. In 1962, he briefly had a deal at Sunbeam Music, which published some of his songs, followed by a stint at Roosevelt Music. While he was there, an assignment came in from Dot Records to submit a follow-up to Pat Boone's novelty hit "Speedy Gonzales." Ten of the firm's writers eventually collaborated on a song, appropriately called "Ten Lonely Guys," which Boone recorded, and which reached number 45 in the Billboard Hot 100 in October 1962. Diamond, one of the ten, was credited under the pseudonym Mark Lewis, but this was his first appearance in the charts. (He also sang lead on the demo, and it has been suggested that the Diamond Records single of "Ten Lonely Guys," credited to Ten Broken Hearts, features his vocals. In 1993, he placed a new recording of the song on his album Up on the Roof: Songs from the Brill Building.) Also in 1962, his composition "Santa Santa" was recorded by the Rocky Fellers and released by Scepter Records. But his next career development involved his own performing. In early 1963, he was signed to a singles deal by Columbia Records, and on January 24th, his 22nd birthday, had his first solo recording session, followed by a second session three months later. The results emerged on July 2 as Columbia single 42809, "Clown Town"/"At Night," his first solo release. (Both tracks appeared on In My Lifetime.) Unfortunately, the record flopped, and he was dropped by the label.

Recently married to schoolteacher Jay Posner (with whom he had two daughters), Diamond kept plugging away, even opening his own tiny office above the jazz club Birdland in midtown Manhattan. In early 1965, his song "Just Another Guy" was recorded in the U.K. by Cliff Richard and placed on the B-side of the number one single "The Minute You're Gone," released on the British Columbia label. In February 1965, he met the successful writers and producers Jeff Barry and Ellie Greenwich, who took an interest in him and got him signed to songwriter/producers Jerry Leiber and Mike Stoller's Trio Music publishing company for three months. This association was over by the time Leiber and Stoller had one of their clients, Jay & the Americans, record "Sunday and Me," a song Diamond had written at Trio. Released as a single in the fall of 1965, the song peaked at number 18 in December, giving him his first real hit as a songwriter. By then, he had made other progress in his career. On June 25, he signed a deal with Barry and Greenwich for publishing and recording, the three forming Tallyrand Music with Diamond as president. (This appears to have prompted his decision finally to drop out of NYU.) Tallyrand shopped both Diamond's songs and Diamond as a recording artist, and on January 6, 1966, it signed a contract with WEB IV, the company controlling the independent Bang Records label. Soon after, Diamond was back in a recording studio, and on April 4, Bang released his label debut single, "Solitary Man," produced, as all his subsequent Bang discs would be, by Barry and Greenwich. "Solitary Man" gave him his first chart entry as a recording artist, peaking at number 55 on the Hot 100 in July. (In 1970, T.G. Sheppard revived it for a number 14 country hit. Among numerous other covers over the years, the song has been placed on chart albums by the Sidewinders, Chris Isaak, and Johnny Cash, appearing as the title song on Cash's 2000 release American III: Solitary Man.)

Diamond quickly followed "Solitary Man" with his second Bang single, "Cherry, Cherry," released in July 1966, which gave him his first substantial hit, peaking at number six in October. (The many covers of the song include one quickly cut by the hard rock group the Music Machine for its chart LP [Turn On] The Music Machine.) The single's B-side, "I'll Come Running," was covered by Cliff Richard, who scored a Top 40 hit with it in 1967. When song publisher Don Kirshner heard "Cherry, Cherry," he called Diamond into his office and asked if the songwriter had a similarly upbeat tune that could be used by the Monkees, a group put together for an upcoming TV series. Diamond played him "I'm a Believer," a song intended for his debut album. Kirshner liked it, and Diamond, Barry, and Greenwich recorded a backing track that Kirshner took to California and had the Monkees sing over. By the time "I'm a Believer" was released as the Monkees' second single in the fall of 1966, the group was a teenybopper phenomenon, and the disc had advance orders of over one million copies. It shot to number one, where it stayed seven weeks, becoming the biggest single of 1967. (Among many covers, "I'm a Believer" appeared on chart albums by the Four Tops and the Ventures in 1967. Tommy Overstreet revived it for a number nine country hit in 1974, the same year Robert Wyatt took it into the U.K. Top 40. EMF and Reeves and Mortimer hit the British Top Ten with it in 1995. In 2001, it was revived by Smash Mouth in the movie Shrek and reached number 25 in the U.S.)

Diamond's debut LP, The Feel of Neil Diamond, released in August 1966, was a rush job, featuring "Cherry, Cherry" and "Solitary Man" along with his covers of hits like "La Bamba" and "Monday, Monday." It barely charted. Also featured, however, was "I Got the Feelin' (Oh No No)," an original composition that would be his next single in October. It reached number 16 in December, but the 45 was also significant for its Diamond-penned B-side, "The Boat That I Row." British singer Lulu quickly covered the song, and her version became a Top Ten U.K. hit in the spring of 1967. Diamond's fourth Bang single, "You Got to Me," was released in December 1966 and peaked at number 18 in March 1967. In February, his song "Look Out (Here Comes Tomorrow)" was featured on the Monkees' chart-topping second album, More of the Monkees. The following month, "A Little Bit Me, a Little Bit You," the Diamond-penned follow-up to "I'm a Believer," entered the singles chart for the Monkees; it peaked at number two in April. Also in March, Bang released its fifth Diamond single, "Girl, You'll Be a Woman Soon," which became his second Top Ten hit in May. (Among the many covers of this dark ballad, the most famous was the one by Urge Overkill, which the band recorded for its Stull EP, after which it was used in the film Pulp Fiction and released as a single, reaching number 59 in 1994.) In April, Ronnie Dove entered the charts with "My Babe," written and produced for him by Diamond; it peaked at number 50 in May. Bang's sixth Diamond single, "Thank the Lord for the Night Time," appeared in June, peaking at number 13 in August. That month saw the release of Diamond's second LP, Just for You, which peaked at number 80. Diamond's sixth Bang single, "Kentucky Woman," followed in September, and it reached number 22 in November, giving him his sixth consecutive Top 40 hit. ("Kentucky Woman" has proven to be one of Diamond's more versatile songs. Hard rockers Deep Purple peaked at number 38 with their cover in 1968, while Randy Barlow revived it for a number 26 country hit in 1977.)

After nearly two years of hit recording and songwriting, Diamond had a falling-out with his producers and his record label. As popular music turned more serious in the late '60s, he became less satisfied writing simple pop songs, and, instead of "Kentucky Woman," he had proposed that his sixth Bang single be "Shilo," an introspective ballad not about the Civil War battle, but about an imaginary childhood friend, that he had written and recorded. Bang, thinking the song less commercial than "Kentucky Woman," used it as an LP track on Just for You instead, and Diamond, who was also dissatisfied with his royalties, found a loophole in his contract, which, it turned out, failed to bind him exclusively to WEB IV and Tallyrand. He therefore declared himself free to sign a recording contract with another company. Soon, lawsuits were flying. Meanwhile, Bang was reduced to issuing a cover of Gary "U.S." Bonds' "New Orleans," previously released on The Feel of Neil Diamond, as its next Diamond single in December 1967; the disc peaked at number 51 in February 1968. In March, the label followed with a moody ballad called "Red Red Wine" culled from Just for You. It peaked at a disappointing number 62 in April, but the song has had considerable life since. It was quickly taken up by Jimmy James & the Vagabonds, whose cover was a Top 40 U.K. hit later in 1968. The following year, Jamaican artist Tony Tribe also had a British chart entry with it. Vic Dana gave it another run on the U.S. pop charts in 1970, and Roy Drusky reached the country Top 20 with it in 1971. In 1983, UB40, preparing their Labour of Love album of reggae covers, recorded a version based on the Tony Tribe treatment, unaware it had been written by Diamond. Released as a single, this recording hit number one in the U.K., earning a Top 40 placing in the U.S. in early 1984. Then, in 1988, the song was re-released after being revived by a disc jockey and topped the American charts.

Professionally, Diamond tried to stem the tide of his career decline by recording at American Sound Studio in Memphis, beginning on January 8, 1969. Working with producers Tommy Cogbill and Chips Moman, he took more of a gospel-tinged, country-rock approach, starting with the single "Brother Love's Travelling Salvation Show," quickly released as a single, which peaked at number 22 in April, his best chart showing in 18 months. (The song didn't attract many cover versions, although Peggy Lee put it on her Is That All There Is? album later in the year. But it became very familiar to Diamond fans as his traditional concert closer.) He quickly returned to Memphis and cut an album also called Brother Love's Travelling Salvation Show that was released in April and peaked at number 82. Among the album's songs was "And the Grass Won't Pay No Mind," which Elvis Presley cut for his From Memphis to Vegas/From Vegas to Memphis LP later in 1969, after which Mark Lindsay recorded it for a single that reached number 44 in 1970. But the song that sealed Diamond's commercial comeback was his next single, "Sweet Caroline (Good Times Never Seemed So Good)," a catchy tune that peaked at number four in August, the same month it earned a gold record certification for sales of one million singles. (Starting in February 1971, Uni added the track to issues of Brother Love's Travelling Salvation Show, which eventually earned its own gold record certification for sales of 500,000 LPs.) It also became Diamond's first single to place on Billboard's Easy Listening (later Adult Contemporary or AC) chart, where it peaked at number three. Eventually, it earned a platinum record certification for sales of two million singles. (The song was widely covered by other artists. In 1970, Anthony Armstrong took it into the Top 40 of the country charts. In 1972, Bobby Womack took it into the Top 20 of the R&B charts. And it has appeared on chart albums by Andy Williams, Bobby Goldsboro, Elvis Presley, the Ventures, Ray Conniff, Boots Randolph, Frank Sinatra, and Waylon Jennings.) Diamond followed "Sweet Caroline" with the gospel-tinged "Holly Holy," released in October 1969, and scored another big hit, the track peaking at number six in December. It was his second gold (and eventually platinum) single, and the song earned a cover by Junior Walker & the All-Stars that made the R&B Top 40 in 1971. The Diamond recording was included in his fifth LP, Touching You Touching Me, released in November 1969; the disc was his most successful so far, peaking at number 30 and going gold in a little over a year.

Meanwhile, Diamond's career resurgence was not going unnoticed at his former label, Bang Records. Heretofore, Bang had contented itself with reissuing its small catalog of Diamond's recordings, but it now took a more aggressive stance by having the American Sound Studio musicians record a new musical track for "Shilo" under Diamond's vocal to create a sound more like his current records. This heavily overdubbed version of "Shilo" was released as a single in January 1970, and it reached number 24 in April. Diamond responded by returning to Memphis himself and cutting a new recording of "Shilo," which was added to later editions of Velvet Gloves and Spit. His next single, a cover of Buffy Sainte-Marie's "Until It's Time for You to Go," which had appeared on Touching You Touching Me, was released in February and peaked at number 53 in March. A more ambitious effort was "Soolaimón (African Trilogy II)," released in April, an excerpt from the side-long "folk ballet" of African-styled songs to be featured on his next album, Tap Root Manuscript, in the fall. The single reached number 30 in May. It was outpaced, surprisingly, by Bang's re-release of "Solitary Man," which peaked at number 21 in September. Thankfully, that redundant product did not slow the success of Diamond's next new single, "Cracklin' Rosie" (famously referring to the cheap wine Cracklin' Rosé), which was released in July and became his biggest hit yet, topping the charts in October, when it was certified as his third gold single. (It eventually went platinum.)

Also released in July 1970 was the live album Gold, which had been recorded in March at the Troubadour nightclub in Los Angeles. Containing new versions of "Solitary Man," "Cherry, Cherry," "Kentucky Woman," and "Thank the Lord for the Night Time," the album was interpreted by some as an attempt to provide versions of the highlights of the Bang catalog for Diamond's current label. But it also made the claim for the singer as an exciting live performer, and it was a major commercial success, peaking at number ten in September and becoming his first LP to be certified gold. (It has since been certified double platinum.) As the result of "Cracklin' Rosie" and Gold, by the fall of 1970 Diamond had graduated to the theater and arena circuit as a live act. (He also broke internationally, as "Cracklin' Rosie" went Top Ten in the U.K.) For his next single, he made the odd choice of releasing a cover of "He Ain't Heavy, He's My Brother," a song that had been a Top Ten hit for the Hollies the previous spring. Competing with Bang's release of the former B-side "Do It," it still managed to peak at number 20 in December and, along with "Soolaimón" and "Cracklin' Rosie," served as a good calling card for Tap Root Manuscript, which appeared in November. Consistent with Diamond's current status, the album peaked at number 13 and went gold in two months.

Reportedly, Diamond worked months on the lyric of his next single, the autobiographical "I Am...I Said," released in March 1971. An impassioned statement of emotional turmoil, the song was very much in tune with the confessional singer/songwriter movement of the time, and it became a major hit, peaking at number four in May, with even its B-side, "Done Too Soon" (previously released on Tap Root Manuscript), earning a chart placing. "I Am...I Said" earned Diamond his first Grammy nomination, for Best Pop Vocal Performance, Male. (Personal as the song may have seemed, Bill Phillips covered it for a country chart entry in 1972.) Diamond did not have another new release for seven months, although Bang once again presented one of its overdubbed efforts when it released an altered version of "I'm a Believer" in May and saw it reach number 51. Finally, Diamond returned to the record racks in the fall with the ballad "Stones," released in October, followed by an album of the same name in November. The single reached number 14, while the LP stopped just short of the Top Ten and went gold in two months.

Diamond's next album, Moods, was prefaced by another of his standards. "Song Sung Blue," released in April 1972, became his second number one hit on the Hot 100 in July, also becoming his fourth gold single and earning Grammy nominations for Record of the Year and Song of the Year. As a song, it was covered by many artists, quickly recorded on chart albums by Vikki Carr, Ray Conniff, Percy Faith, Johnny Mathis (the LP itself called Song Sung Blue), Wayne Newton, Bobby Vinton, Andy Williams, Cal Smith, and Frank Sinatra. Moods, which followed in June, peaked at number five in September, a new high for Diamond, and went gold in two months. (It later went platinum.) Its success, which included a Grammy nomination for Album of the Year, was augmented by the subsequent release of the singles "Play Me" (number 11 in October) and "Walk on Water" (number 17 in December). In August, Diamond performed ten shows at the Greek Theatre in Los Angeles, recording them for a live album. The double-LP set Hot August Night, which appeared in November, cemented his status as a concert attraction by hitting number five and going gold in a month. (It was later certified double platinum.) A single of "Cherry, Cherry" was excerpted from the release and made number 31.

Hot August Night marked Diamond's ascension to superstar status, and it also marked the end of a phase of his career. After three weeks of shows at the Winter Garden on Broadway in October, he temporarily retired from live performing. At the same time, he had completed his recording contract, and he signed a new, lucrative one with Columbia Records. His first project for the new label was a song score for the film version of the best-selling novel Jonathan Livingston Seagull. It was a troubled project, and by the time the movie was released in October 1973, both Diamond and Richard Bach, the book's author, were suing the film producer. Reviews were awful, and the picture bombed. But Diamond's score, released as a solo album by him, was a hit. The single "Be" only grazed the Top 40, yet the LP reached number two in December, having gone gold upon release. (It has since gone double platinum.) It also won Diamond the 1973 Grammy Award for Best Album of Original Score Written for a Motion Picture or TV Special. "Skybird," the second single drawn from the LP, made the charts and was covered by Dawn for another chart single in 1975.

Even after completing Jonathan Livingston Seagull, Diamond continued to stay off the road. He was next heard from in the fall of 1974, when he released his first regular album for Columbia, Serenade, prefaced by the single "Longfellow Serenade," which was his biggest hit since "Song Sung Blue," peaking at number five on the Hot 100 and number one on the AC chart in November. Serenade hit number three in December, another instant gold album that has since gone platinum. Follow-up single "I've Been This Way Before" barely made the Top 40 on the pop chart, but topped the AC chart, a good example of the increasing dichotomy between the success of Diamond's 45s on the two charts. (A third single, "The Last Picasso," went Top Ten AC but missed the Hot 100 entirely.)

Another year went by before Diamond finally returned to live work, doing a few shakedown shows in California and Utah in late January and early February 1976 before launching a tour of Australia and New Zealand, followed by more dates in the U.S. in the spring. Meanwhile, working with Malibu, CA, neighbor Robbie Robertson of the Band as his producer, he had finished a new album, Beautiful Noise, its songs reflecting back on his early-'60s days in Tin Pan Alley. Leadoff single "If You Know What I Mean," issued in June, reached number 11 on the Hot 100 and number one on the AC chart. The album, which followed a couple of weeks later, hit number four, as usual going gold on release, with one of the newly introduced platinum certifications following in September. Follow-up singles "Don't Think I Feel" and "Beautiful Noise" went Top Ten AC. On July 1, 1976, for a hefty fee, Diamond made his Las Vegas debut at the Aladdin Hotel, though he would avoid the entertainment mecca afterward until well into the '90s. In September, he returned to the Greek Theatre in Los Angeles, this time with both cameras and recording equipment in tow. On November 25, 1976, he appeared as one of the special guests at the Band's farewell concert at Winterland in San Francisco, performing the Beautiful Noise track "Dry Your Eyes," which he had co-written with Robertson. The show was filmed and recorded for the 1978 movie and triple-LP set The Last Waltz.

Both of Diamond's albums of 1977 were associated with television specials. First came Love at the Greek, like Hot August Night a two-LP concert set drawn from shows at the Greek Theatre. It appeared in February 1977, two weeks ahead of The Neil Diamond Special, broadcast February 21. The LP reached number eight in April, selling a million copies by July, with another million registered since. Diamond undertook a lengthy tour of Europe in the spring and summer. While he was now writing almost exclusively for himself, one of his cast-offs, a song called "Sunflower," was recorded by Glen Campbell, who took it into the country Top Ten and the pop Top 40 in August. In November, Diamond was back with a new studio album, I'm Glad You're Here with Me Tonight, again tied into a TV special. The simultaneously released single "Desirée" went Top 20 pop and number one AC, while the album reached number six in February 1978, racking up the usual sales number of a million copies with another million to come. Interestingly, Columbia released the title song as a second single that missed the charts entirely, while ignoring both "Let Me Take You in My Arms Again," which James Darren recorded for a country chart entry, and a sad breakup ballad called "You Don't Bring Me Flowers" that Diamond had written for a television pilot about reversed sex roles (hence the novelty of having a man complain about romantic neglect in terms usually used by a woman). Labelmate Barbra Streisand, however, knew a big ballad when she heard one, especially one co-written by her personal lyricists, Alan and Marilyn Bergman, and she quickly covered the song, which appeared on her Songbird album in May 1978. A disc jockey, realizing that both Diamond's and Streisand's versions were in the same key, spliced them together and began playing on the air the duet he had created, leading to requests for a record. On October 17, 1978, that desire was satisfied, as the two singers cut a new recording of the song. Credited to "Barbra & Neil," the single was quickly released and soared to number one on the pop charts, eventually earning a platinum certification. (Grammy nominations for 1978 Song of the Year and 1979 Record of the Year followed. Of course, "You Don't Bring Me Flowers" quickly became a standard. Jim Ed Brown and Helen Cornelius cut it for the country market and enjoyed a Top Ten hit.)

Diamond had been working on an album to be titled after a tune called "The American Popular Song," written by his pianist, Tom Hensley; the LP was to be a collection of covers. The unexpected success of the duet upset these plans, however, and Diamond quickly cobbled together an album for release under the title You Don't Bring Me Flowers, which appeared in November. By the end of January, it peaked at number four, having been certified platinum, with a double platinum award to follow. In February, Columbia released another single from it, the up-tempo "Forever in Blue Jeans" (co-written by Richard Bennett), which reached the Top 20. "Say Maybe," following in April, was less successful though, as usual, it reached the Top Ten of the AC chart. (Meanwhile, in December 1978, Diamond made another of his rare forays into the movies, contributing the song "I Seek the Night" to the soundtrack of the Clint Eastwood film Every Which Way But Loose, where it was sung by Sondra Locke.)

Diamond collaborated with French singer/songwriter Gilbert Bécaud on the title track of his next album, September Morn, released in December 1979. The single reached the Top 20 of the pop chart, and the album peaked at number ten in February 1980, selling a little more slowly than previous releases, though it was platinum by May and has since sold another million copies. Any thought that Diamond's popularity might be cooling, however, was belied by his next project. Almost without acting experience, he had nevertheless agreed to star in a second screen remake of The Jazz Singer. The response was very similar to what had greeted Jonathan Livingston Seagull seven years earlier, except that this time Diamond was actually in the picture. Upon release in December 1980, it was panned by critics and became a box office failure. But the Capitol Records soundtrack album, consisting of a Diamond-written and performed song score, was a remarkable hit. "Love on the Rocks" (co-written with Bécaud) came out in advance of the LP, and it peaked at number two in January 1981, held out of the number one spot by the recently murdered John Lennon's "(Just Like) Starting Over." By February, the album was up to number three, having already sold a million copies. "Hello Again" (co-written by Alan Lindgren of Diamond's band), the second single, reached number six in March, and the anthemic "America" peaked at number eight (number one AC) in June as the album kept selling. (Eventually, it was certified for sales of five million copies, making it Diamond's most successful LP. It earned him another Grammy nomination in the category of Best Album of Original Score Written for a Motion Picture or TV Special.)

Diamond picked a good time to reach a career peak: His record contract was up for renewal, and he re-signed to Columbia Records in October 1981 committing himself to ten more albums at a guarantee of 30 million dollars. It was, briefly, the most lucrative record contract in history. At the same time, of course, he had a new Columbia album ready, On the Way to the Sky, advanced by the single "Yesterday's Songs," which topped the AC chart and reached number 11 in the pop chart. The album, however, became his first in ten years to miss the Top Ten, peaking at number 17. The title track, co-written with Carole Bayer Sager, failed to chart as a 45, but a third single, "Be Mine Tonight," made the Top 40. Having worked with Bayer Sager, Diamond now turned to collaborating with both her and her then-husband, Burt Bacharach, a fellow graduate of the Brill Building era, on his next album, Heartlight. The title song, written by the three and inspired by the recently released movie E.T.: The Extra-Terrestrial, emerged in August 1982 as a single that hit number one in the AC chart and returned Diamond to the pop Top Ten, peaking at number five in November. That helped the album to a number nine peak the same month, and by the end of the year it had become his eighth consecutive new album to be certified platinum. Second single "I'm Alive" (co-written by Diamond and writer/producer David Foster) reached the Top 40, and a third single, "Front Page Story" (another Bacharach/Bayer Sager/Diamond composition), also charted.

Diamond was relatively inactive on the performing front in 1983, though he did undertake a week-long series of shows at the Forum in Los Angeles in June, his first L.A. shows in six years. He was, of course, writing, again collaborating with Bacharach and Bayer Sager, and recording, and on February 6, 1984, he submitted a new album to Columbia. The label asked him to make changes and, citing the artistic control mandated in his contract, he sued to have the LP released as it was. In April, however, he withdrew his suit and revised the disc to the record company's requirements. After completing the new version, he accepted a 500,000-dollar fee for performing three shows at Harrah's Trump Plaza in Atlantic City, NJ, in June, then undertook a European tour, followed by an American tour. Columbia released the new album, Primitive, in July, along with the first single, "Turn Around" (co-written by Diamond, Bacharach, and Bayer Sager). Notwithstanding the label's attempt to enhance the commerciality of the disc, it was a disappointing seller. "Turn Around" lodged in the AC Top Ten, but missed the pop Top 40, and Primitive peaked at number 35 and only went gold, the worst showing for a new Neil Diamond album since 1969. Two follow-up singles only made the lower reaches of the AC chart.

Diamond reacted by working up what was intended to be one of his most personal albums, as indicated by its proposed title, The Story of My Life. He submitted the collection to Columbia in September 1985, and for the second time in a row had an album rejected by the label. This time, he did not protest publicly. Instead, he accepted Columbia's suggestions that he try to take a more contemporary approach by, for example, working with Maurice White of Earth, Wind & Fire, recording a song written by currently popular rocker Bryan Adams, and using such guest stars as Stevie Wonder (who also co-wrote a song). Eventually, every song on the album except the former title track, "The Story of My Life," was replaced. To further promote the upcoming release, now titled Headed for the Future, in January 1986 Diamond taped a new television special, Hello Again, for CBS, then the parent company of Columbia Records. The special was broadcast May 25, two and a half weeks after the release of Headed for the Future, which itself had been prefaced by the release of the title song (written by Diamond, Hensley, and Lindgren) as a single in late April. The effort to modernize Diamond succeeded only slightly. The album peaked at number 20, an improvement over Primitive, but like its predecessor, the album only went gold. The single missed the Top 40, and a second single, "The Story of My Life," got to only number 11 AC.

But if his record sales were disappointing, Diamond's concert tours remained SRO. An eight-night stand at Madison Square Garden in New York was followed by 14 shows back at the Greek Theatre in August, commemorated by Columbia with another double-LP live album, Hot August Night II, released in October 1987. The album, however, peaked at a disappointing number 59 and didn't even go gold at first (though it has since gone platinum). (Appended was a studio recording of "I Dreamed a Dream" from the musical Les Misérables, which got to number 13 on the AC chart.)

Diamond's main collaborator for his next studio album, The Best Years of Our Lives, was David Foster, who produced it and co-wrote several of the tracks. Released in December 1988 to coincide with an HBO special, the album peaked at number 46 and went gold, with three of its tracks making the AC chart. Much the same response greeted Diamond's next studio album, Lovescape, produced by Peter Asher (the famed producer of James Taylor and Linda Ronstadt, who began to work with Diamond regularly), when it appeared in August 1991. It peaked at number 44 and spawned three AC chart entries, while taking almost three years to go gold. Meanwhile, however, Diamond remained a major force on the concert circuit, taking his Love in the Round tour around the country and around the world. In 1992, for example, he was said to be the second-highest grossing American concert act of the year. Given this continuing appeal, he and Columbia hit upon a new strategy for his record releases. For the time being, they suspended the usual practice of having him simply write and record a new studio album every year or two. Instead, they embarked on a series of special releases that focused on his status as a veteran singer. The Greatest Hits (1966-1992), released in June 1992, was a double CD spanning the Bang era and the Columbia hits, with the Uni material represented by recent live recordings; by 2000, it had gone triple platinum. In September 1992, Diamond released his first seasonal collection, The Christmas Album, and promoted it with Neil Diamond's Christmas Special on HBO. The album peaked at number eight in December, his first Top Ten LP in ten years. Within a year, it was platinum, with another million registered by 2001.

In January 1993, Diamond again re-signed to Columbia for an additional six albums. The first of these, released in September, was Up on the Roof: Songs from the Brill Building, his treatments of early-'60s evergreens like the title song and "You've Lost That Lovin' Feelin'." It hit number 28 and went gold. Meanwhile, the singer continued to tour extensively, his grosses for the year exceeded only by U2. That success was reflected by yet another concert recording, Live in America, a double CD issued in June 1994 that peaked at number 93 and eventually went gold. The fall brought The Christmas Album, Vol. 2, only two years after its successful predecessor; it peaked at number 51 and quickly went gold. (Also in the fall of 1994, Diamond participated in the Frank Sinatra album Duets II, singing "The House I Live In" with the venerable star.)

During 1995, Diamond finally got to work on an album of newly written material, but there was a twist. The man whose songs had sometimes been turned into country hits went to Nashville and held songwriting sessions with country writers, also recording with country stars. The result was Tennessee Moon, released in February 1996, along with a TV special, Under a Tennessee Moon, broadcast on ABC. The album peaked at number three in the country charts and number 14 in the pop charts and went gold. Next, Columbia released In My Lifetime, a three-CD box set retrospective, in October 1996, including Bang, Uni, and Columbia hits, along with demos and other rarities and unreleased material. The album charted, a relative rarity for box sets, and went gold. Diamond continued to make events out of his album releases. In October 1998, he issued The Movie Album: As Time Goes By, a two-disc collection of covers of movie songs like "Moon River" and "Unchained Melody." It reached number 31 and went gold, earning a Grammy nomination for Best Traditional Pop Vocal Performance. As usual, Diamond embarked on a world tour to support it. And as usual, his fans came out. Even during a decade when he retreated from the frontline of recording artists, the singer's live following, if anything, increased. He was named the top solo concert artist of the 1990s by Amusement Business magazine.

Diamond's appeal to audiences was reflected humorously in the film Saving Silverman, featuring a self-spoofing appearance by the singer, which opened in February 2001. More seriously, he finally wrote and recorded a new studio album, Three Chord Opera, released in July 2001. In fact, he did all the writing entirely by himself, the first time he hadn't collaborated with anyone since Serenade in 1974, which gave Columbia a promotional tag to bill the album as another "event" release. Considered as his first regular studio album since Lovescape in 1991, the disc was Diamond's highest-charting release of this sort since Heartlight in 1982, peaking at number 15 and quickly going gold. In December 2001, Columbia's Legacy division released The Essential Neil Diamond, a new two-CD retrospective, and by 2005 it was a platinum seller. The fall of 2003 brought a massive five-CD/one-DVD set, Stages: Performances 1970-2002, which sold well enough to spend a couple of weeks in the chart as Diamond undertook yet another lengthy tour. In 2004, he began working with renowned producer Rick Rubin, a longtime fan who had produced Johnny Cash's 1990s comeback albums, including American III: Solitary Man. Before releasing the result of their collaboration, the 2005 album 12 Songs, he embarked on another world tour. 12 Songs was issued on November 8, 2005, to a chorus of positive reviews. It entered the chart at number four, Diamond's highest chart placing in 25 years, but its longer-term success was short-circuited because of Columbia's decision to include anti-copying software on the CDs. The software was thought to damage personal computers, and many of the discs had to be recalled, hurting Diamond's sales, although the album was certified gold. In 2006, Diamond made another movie cameo, singing "Hava Nagilah" in the film comedy Keeping Up with the Steins, and he returned the recording studio with producer Rick Rubin for 2008's Home Before Dark. Released May 6, 2008, Home Before Dark entered the Billboard chart at number one for the week ending May 24, 2008, Diamond's first-ever chart-topping album. A holiday release, A Cherry Cherry Christmas, appeared in 2009.

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