Magazine Feature

The Inside Story Behind the Making of Frank Sinatra's Ambitious and Wacky 1980 Three-Disc Album, 'Trilogy'

Frank Sinatra in a recording studio in 1979.
Ed Thrasher/

Frank Sinatra in a recording studio in 1979.

Frank Sinatra, a man not fond of interruption, was in the middle  of a 1978 recording session at Warner Bros. studios in Burbank when his longtime producer Sonny Burke walked in and dared to halt the proceedings. Vincent Falcone, a pianist-conductor who had worked with Sinatra for two years at that point, recalls that the singer, then 63, was recording Cy Coleman’s “I Love My Wife.” Falcone doesn’t remember if the song was intended for a new album -- Sinatra had already recorded it as a single -- but whatever the purpose of the session, Burke thought he had a better idea.

Burke ushered Sinatra into the control room, and an animated conversation ensued. “They were in there for quite a while,” remembers Falcone. “When the boss came out, he just said, ‘That’s it. We’re not going to do anything else until I do this project.’ He sent everybody home.”  

Ron Galella/WireImage
Dean Martin and Frank Sinatra in concert at Resorts International Hotel in Atlantic City, NJ. 

“This project,” a triple album eventually titled Trilogy: Past Present Future, would employ 200-plus musicians and backup singers, and take more than a year to complete. And 35 years after its March 1980 release, in this, the year of Sinatra’s 100th birthday, it remains one of the most ambitious, strange, brilliant and bloated albums of his or any other artist’s body of work.

Frank Sinatra Podcast: Filmmaker Alex Gibney, Biographer James Kaplan Talk HBO Doc & More

Comprising standards, contemporary songs and new material written expressly for Sinatra, the set was intended to be a summation of his work to that point and, in its odd way, succeeds, containing the multitudes that were Sinatra, the artist: the wonderful, the less wonderful, the lapses in taste and, on the album’s notorious third disc, the most spectacular misfire of his career.

“It’s a conspicuous album. And a deeply problematic one,” says author James Kaplan, whose Sinatra: The Chairman, the second installment of a definitive two-volume biography, will be published Oct. 27.  

“Conspicuous” is a good adjective for Trilogy -- less so for Sinatra’s recording career in the late ’60s and ’70s. While he remained a huge concert draw, his albums, on which he grappled with pop-rock material, were met with ambivalence. It must have been disheartening for a singer who cherished record sales as much as he cherished the works of Jerome Kern, Cole Porter, and Irving Berlin to bluff his way through the likes of Petula Clark's hit single, “Don’t Sleep in the Subway,” and Kermit The Frog’s signature song, “Bein’ Green,” and yet barely graze the charts. Sinatra even toyed with “retirement” for a couple of years in the early ’70s, but as his son, Frank Sinatra Jr., puts it, “He decided playing golf and sitting around drinking pink tea was not for him.” Nevertheless, his 1974 LP, Some Nice Things I’ve Missed, would be his last studio album for six years.  A few aborted LPs and several singles followed; the last thing Sinatra released before Trilogy was a disco version of “Night and Day,” a 45 that came and went in 1977 and is every bit as depressing as it sounds

Rewinding the Charts: In 1967, Frank & Nancy Sinatra Shared a No. 1

Not that Sinatra had given up. “When we were in the recording studio, he was experimenting more than anything else,” says Falcone. “He was trying to come up with something that would be worthy of a recording.” As the singer told the New York Daily News in 1978, “There is good music around. We look every day.” He said he sometimes rang up songwriter friends in hopes of cadging new tunes, but the responses were discouraging. “They say, ‘What the hell good is it; nobody will do it. It’s only kid music today.’ ” The singer concluded, sounding half-resigned, “Maybe I should get more [young] songwriters to come and see me.”

Trilogy lit a new fire under him, according to Falcone: “When Sonny brought the project in, that really turned Mr. S on.” Burke, who had been Sinatra’s producer since 1965, was looking for a way to mark the singer’s 40th anniversary in show business (dating from his first recording, in 1939, with Harry James’ band). His brainstorm was a three-disc “recapitulation” of Sinatra’s career, originally titled The Sinatra Trilogy. “That was Sonny’s baby from day one. He poured his heart and soul into it,” says Sinatra Jr.  

Each record was to be an album unto itself.The Past: Collectibles of the Early Years, the first LP’s formal title, consists of 10 pre-rock standards, seven of which Sinatra had not formally recorded before, including "My Shining Hour" and “They All Laughed.” The hope was that Nelson Riddle -- the arranger who had guided Sinatra toward the more relaxed but commanding style that revived his career in the mid-1950s via such albums as Songs for Swingin’ Lovers! -- would take the gig. But the singer had bruised Riddle’s feelings by being unable or unwilling to attend a fundraising dinner in Riddle’s honor, even after it was rescheduled in an effort to accommodate Sinatra. “Nelson was terribly hurt,” says Falcone, and in no mood to lend a hand. “Tell him I’m busy,” Riddle told Falcone over the phone, and hung up -- to which Sinatra replied, “Who needs him,” with an added expletive or two.

Frank Sinatra to be Honored at 2015 Architects of Sound Awards in L.A.

Sinatra had actually committed a double faux pas, according to Michael Feinstein, the singer, American Songbook scholar and cabaret impresario. (He recently became a partner in the Manhattan nightclub Feinstein’s/54 Below.) Feinstein was friendly with Riddle, who, when Feinstein asked about Trilogy, said he would have considered arranging The Present or The Future, despite his anger at Sinatra, but “took offense” at being asked to do The Past, as if he were strictly yesterday. (Then again, Riddle didn’t look down his nose at arranging an album of standards for Linda Ronstadt the following year.)

As second choices go, Billy May, with whom Sinatra had collaborated on some of the hardest-swinging LPs of his career, including Come Dance With Me and Swing Along with Sinatra, was hardly leftovers. His arrangements nodded to Sinatra's big band recordings of the 1940s, and if the one-time "Voice" wasn't quite in vintage shape, he sounded smoother on The Past than he had in years, husky at time but with less of the bark and bite of his "My Way" era. According to Falcone, he had quite smoking a year before the July 1979 sessions, going into "training" for the album, as Kaplan puts it. 

Both Falcone and Sinatra Jr. remember singer, musicians, and arranger all enjoying themselves in the studio. “We had a great time,” says Falcone. “When we did things like ‘They All Laughed,’ and Sinatra told the band to laugh at the end of the recording -- that was something he came up with when we were in the studio -- we loved it.” Indeed, the pleasure of all concerned is audible in the record’s buoyant grooves: Sinatra singing the kinds of songs he was born to sing. People noticed. Feinstein, who was working for Ira Gershwin at the time as an archivist, remembers that the songwriter “was very proud of the fact that he was the only songwriter with two songs on The Past‘But Not for Me’ and ‘They All Laughed.’ That meant something to him because Sinatra of course mattered greatly to Ira.”

Frank Sinatra's Billboard Chart History

The songs on disc two, The Present: Some Very Good Years, were intended to be more of the moment, with recenti-ish numbers from the likes of Billy Joel and Neil Diamond. along with "Love Me Tender," already a chestnut in 1979. The arranger for all but one song was Don Costa, who first worked with Sinatra on the sublime 1962 Sinatra & Strings but had since shouldered many of the singer’s “youth will be served” efforts (as Falcone remembers Sinatra once putting it). Not surprisingly, The Present, recorded mostly in New York in August 1979, is a mixed bag. Sinatra sings George Harrison’s “Something” with care and genuine yearning, but ultimately brings too much horsepower and a few ham-fisted Vegas-isms (“You stick around, Jack, it might show”) to what is, in essence, a folk song.  And yet, when the material was right for him, as was the case with John Kander and Frank Ebb’s “Theme From New York, New York”— Trilogy’s most enduring track -- Sinatra proved he could still connect. The single, which peaked at No. 32 on the Billboard Hot 100, was his last top 40 hit (as well as the last time he landed a song on that chart) and almost overnight took its place among his most iconic songs.  

Courtesy Photo
Frank Sinatra's "Trilogy: Past Present Future" album cover.

Among Sinatra-philes, Trilogy’s third LP enjoys a more dubious distinction: The singer’s equivalent to The Beatles’ experimental, sprawling rarely listened-to “Revolution 9.” The disc's full title -- The Future: Reflections on the Future in Three Tenses, further enumerated as A Musical Fantasy in Three Tenses for Frank Sinatra, Philharmonic Symphony Orchestra, and Mixed Chorus -- suggests its creators struggled to get a handle on it, too. More oratorio than song suite -- Sinatra referred to it as an “operetta” -- The Future somehow spans a sci-fi lite trip through the solar system, a plea for peace titled “World War None!” and musings on the singer’s life and career. It was written by Gordon Jenkins, who had arranged some of Sinatra’s gloomiest ballad collections beginning with 1957’s Where Are You?

“Frank loved Jenkins, and he loved his nakedly emotional arrangements,” says Kaplan. The arranger’s son, Bruce Jenkins, in his filial memoir, Goodbye: In Search of Gordon Jenkins, cites a letter he discovered from 1959, in which his father pitched Sinatra “a legitimate work for orchestra” he wanted to write that would “capture your entire life and times in music.” This may well have been the seed for The Future, suggesting a December-May marriage between Jenkins’ two-decades-old idea and Burke’s new one, though Bruce doubts this. “Knowing the way my dad worked, I’m sure he didn’t start writing it until it was definitely going to be recorded,” he says. "He worked extremely fast and preferred writing that way."  

20 Great (and a Couple of Not-So-Great) Moments in Singer-Actor History — From Frank Sinatra to Selena Gomez

Falcone, Bruce Jenkins and Sinatra Jr. say they don’t know to what extent Sinatra did or did not shape The Future’s lyrical direction -- "Certainly, they talked," says Falcone -- but the singer was clearly pleased with the  results. In 1980, he told the Los Angeles Herald-Examiner that when a demo tape was first played for him, “I fell down. I said, ‘Holy Christ, how am I going to learn all that stuff? But it put me out the first time I heard it. Really knocked me out.”   

Falcone remembers that he and Sinatra went through extensive rehearsals for the nearly 40-minute long piece. “I would play the melodies for him and record them. I would sit with him, and we would do them over and over. It took about a year for him to learn completely all that material. It’s a huge project, and the music is difficult. He had to learn not only the melodies and the lyrics, but then he had to figure out how he wanted to sing those things. And he’s talking about himself, which is not an easy thing to do.” He adds, contradicting legend, “Mr. Sinatra was not an egotist.”  

The sessions for The Future took place during two days in December 1979, backstage at Los Angeles’ Shrine Auditorium. The venue was chosen for its acoustics and size: An orchestra of more than 140 and a chorus of 50 were assembled for the recording -- surely the biggest session of Sinatra’s career.  “I think he was thrilled to death the huge orchestra and chorus,” says Lee Herschberg, who engineered The Future, as he had many previous Sinatra recordings. “He was never happier than when he was standing in the middle of an orchestra. He was not one to be in a booth or use headphones. He always liked standing right next to the conductor, in this case Gordon, and singing right there on the podium."

TV Review: HBO's Frank Sinatra Documentary 'All or Nothing at All'

Aside from some technical issues synchronizing the huge orchestra and chorus, the sessions went smoothly, though they took a toll on Jenkins, who not long after began showing symptoms of Lou Gehrig’s disease, which would kill him in 1984. “I know it was a tremendous trial for Gordon because I remember how relieved he was after we finished recording,” Herschberg says. “He was under a lot of strain because so much of the responsibility was on him. As we were going out, he was sitting on the apron of the Shrine Auditorium. He was just so relieved it was all over. And he was very happy.”

His mood would not hold, thanks to reactions to the often risible lyrics he wrote for The Future. A sample passage:    

Sinatra: “What time does the next miracle leave?/Let’s get this show on the road/And when the satellite tours begin/Count me in!”

Sinatra and chorus: “Count me in! Count me in!”  

Space station announcer: “Ten, nine, eight, seven, six, five, four, three, two, one.”

Sinatra: “When I arrive at Venus, it will surely be spring/And the girl I have waited for will be waiting for me/And she’ll dance with me all the afternoon/And comfort me when the darkness falls.”  

The Future goes on -- with stops at Saturn, Jupiter and Pluto (where Jenkins manages to rhyme “Hades” with “ladies”) -- and, well, on. It taps a vein that could be  called haute middlebrow, to which singer and composer were both susceptible. Sinatra, after all, had released a 1969 album, A Man Alone, devoted to the proto-New Age songs and poetry of Rod McKuen, and Jenkins had pioneered a series of album-length narrative song cycles such as Manhattan Tower, a bestseller in the early days of long-players, and The Letter, which he wrote for Judy Garland in 1959. Those records -- half light opera, half radio drama -- were hokey enough in their own day and became inexplicably so when Jenkins exhumed the form with The Future and plunked it down in 1980 like a bewildered time traveler. The score's mix of mid-century pop and faux-classical pomp, spiced with the stray Theremin-like sound effect, only added to the feeling that this was a Future more in the vein of Forbidden Planet than Blade Runner

Music-Star Dads and Their Famous Kids

“Frank sort of liked that type of thing, because he felt it gave him wider scope. But I couldn’t make heads or tails of it,” soprano Loulie Jean Norman, who sang on The Future, told Will Friedwald in Sinatra! The Song Is You: A Singer’s Art, the author's indispensable 1997 book on Sinatra's recording career. (Norman knew from science-fiction loopiness, having sung the wordless vocalizations in the original Star Trek theme.) Even Gene Merlino, a singer in The Future's massive chorus who had the additional honor of recording the demos that knocked Sinatra out, concedes ambivalence. “I think some of it was a little bit corny, let’s put it that way.”

Whatever anyone else thought of it, the third disc was clearly meaningful to both singer and composer. As Jenkins told a radio interviewer around the time of Trilogy’s release, The Future was “Frank’s way of saying what he wants to do before -- you hate to say ‘die,’ that’s a tough word -- before he quits.”  

When asked to what extent the singer realized he was going out on a limb, and whether he had any fear that listeners might not follow him, Falcone says, “I can’t imagine there wouldn’t have been a feeling like that. Of course -- that was the challenge. Naturally, Mr. Sinatra wasn’t the kind of person who was going to let everybody know one way or the other how he felt about things -- he was a conservative man -- but I think he was proud of The Future.” Falcone played piano on the recording and recalls Sinatra waiting for him in the parking lot following the last session. “I walked up to him and he put out his hand to me and said, ‘Thanks, kid.’ Then he got into his car and drove away."

An Evolution of Fan Armies  — From Beatlemaniacs to Swifties

One prominent dissenter in Sinatra’s camp was the head of his label, Warner/Reprise. “Mo Ostin was a great money-maker, but he had the aesthetic interest of a fire plug,” says Sinatra Jr. “When Sonny Burke went into his office with this idea for a three-long-player album called Trilogy, Sonny left that office very disconcerted, having been told by Mo Ostin that Warner/Reprise did not want to release Trilogy, because Frank Sinatra had been away from the recording business for too long and the album wouldn’t mean anything.” The singer had hired Ostin in the first place when he founded Reprise as an independent label in 1960 (he had since sold his interest in the merged Warner/Reprise), and he famously didn’t like to be told “no.” But, insists Sinatra Jr., “how they convinced [Ostin] to put Trilogy out, I have no idea.” (Ostin declined to comment.)

From a commercial standpoint, Burke’s faith was proven right. Lavishly packaged, with extensive session notes and a cover featuring a stark sketch of Sinatra printed in black on shiny silver backing, Trilogy peaked at No. 17 on the Billboard 200 and was certified gold by the RIAA, impressive for a triple album. (The Clash’s three-LP Sandinista! --  released that year on Sinatra’s 65th birthday -- only reached No. 24.) 

The reviews, like the album, were all over the map. Los Angeles Times critic Leonard Feather pronounced Trilogy “historic” and “extraordinary.” Writing in Billboard, Dave Dexter Jr. was nearly as enthusiastic, conceding flaws but calling the album “a tour de force that must have left the singer and producer Sonny Burke near exhaustion.” (That was either prophetic or informed: Burke, who had cancer, died less than three months later.) Most everyone, critics and fans alike, was in agreement that The Past was the best thing Sinatra had done in at least a decade and a half, and The Present  had “Theme From New York, New York.” But The Future left most critics baffled. The New Yorker’s Whitney Balliett called it “the silliest venture the singer has ever got himself into,” while Gary Giddins, in The Village Voice, dismissed Jenkins’ lyrics as “inane,” his melodies as “pastiche,” and added, “It’s no fun laughing at Sinatra when he’s working so well.” 

Rewinding the Charts: 25 Years Ago, 'Nothing' Compared to Sinead O'Connor

The criticism devastated Jenkins. As his son wrote, “My father sat at home, crestfallen," his depression abetted by the fact that his beachfront house in Malibu had burned down not long before. Sinatra attempted a more philosophical approach, telling an interviewer, “I’ve been unhappy. Not for myself, because everybody’s been kind to me about the album, but the criticism of the Jenkins piece bothers me. A lot of people around the country don’t understand it. Maybe some smart cookie will come along and do a TV show on it ... I think the lyrics will wear well. They’re too imaginative not to.”

While he waited for that day, Sinatra salved his wounds by cursing out New York DJ Jonathan Schwartz, who had the temerity to tell his listeners that The Future was “narcissistic” and “a shocking embarrassment.” Sinatra then persuaded Schwartz’s station, WNEW, to yank the “f—in’ schmuck” (Sinatra’s words, according to Schwartz’s memoir) off the air for several months. “Alas, I don’t want to talk about Trilogy anymore,” Schwartz now demurs.  

Courtesy of The Jenkins Family
Gordon Jenkins and Sinatra as a "Trilogy" recording session in 1979.

The Past and The Present presaged a brief artistic revival for Sinatra on record. He followed Trilogy in 1982 with She Shot Me Down, a single disc of mostly older songs with arrangements by Jenkins, who would die two years later. On an unconscious level, it may have represented a kind of “do-over” for the two men. “Sinatra knew that Gordon Jenkins was not long for his world,” Falcone says, “and he told me he wanted to pay his respects and that he wanted to give Gordon one last shot.”

Happy 75th Birthday, Billboard Charts!

The resulting disc is an often-overlooked gem in the singer’s catalog, and the last of his albums to be widely admired by devotees, although the album only reached No. 52 on the Billboard 200.  But together, The Past and She Shot Me Down made as prominent a case as there could be in the early 1980s for the continued vitality of the Great American Songbook, and may have helped pave the way for the revival of classic pop as a commercial force. Witness the second act of Tony Bennett’s career -- he lacked a recording contract at the time of Trilogy’s release -- and the popularity of such contemporary jazz-pop singers as Feinstein, Diana Krall, Harry Connick, Jr. and Michael Buble. (The burgeoning number of capable-but-barely standards albums by classic rock acts might be added to the debit side of Sinatra’s ledger.) 

Thirty-five years haven’t exactly redeemed The Future, but time has burnished it with a not-altogether-appalling patina. Bruce Jenkins has wrestled with The Future through the years, trying to hear what his father and Sinatra, who died in 1998, heard in it. Asked to make the best case for the record, he says he would rather direct listeners to the 1965 Sinatra-Jenkins LP September of My Years. Falcone remains proud of The Future. “I was astounded by the whole thing,” he says. “I don’t think there’s ever been an artist that did something like that, not to my knowledge.” No one is arguing. 

An edited version of this article originally appeared in the Oct. 17 issue of Billboard.