The Lessons of Bobby Darin and Dion: Is There Life After Early Stardom?

Every artist who becomes famous as a youngster singing young people’s music sooner or later confronts some difficult questions: How do you keep your music evolving in tandem with your accumulating birthdays? How do you resist the industry’s pressure to stick to a proven formula? And if you do shift to a more mature music, what music is that? Artists such as Taylor Swift, Bruno Mars, Maren Morris and their fellow thirty-somethings are wrestling with those issues now. Dion DiMucci and Bobby Darin had to confront those choices while still in their 20s in the mid-‘60s. How they handled that transition contains some lessons for today’s young stars.

The two men are back in the news. Last year, during the 50th anniversary of Darin’s 1973 death at the age of 37, his estate began rolling out a digital reissue campaign. This featured the seven albums he released between 1966 through 1969—including three of his American Songbook projects and four of his singer-songwriter folk albums. The last of those folk titles—the rarely heard, entirely Darin-written Commitment from 1969—was recently released on vinyl with bonus tracks and deluxe packaging.

Meanwhile, Dion, still going strong at 84, has just released a brand new album, Girl Friends, a collection of blues-rock and country-rock collaborations with female singers such as Shemekia Copeland and Carlene Carter—and also with female guitarists such as Susan Tedeschi and Sue Foley. It’s his 37th album—not including compilations—and it continues the embrace of American roots music he made in the ‘60s.

Darin and DiMucci were both handsome, honey-voiced singers who grew up in the Bronx and had Top-10 rock ‘n’ roll hits in 1959: “Dream Lover” by Darin and “Teenager in Love” by Dion & the Belmonts. These were great recordings, capturing the frustrations and longings of adolescence with luscious vocals that were as rhythmic as they were melodic. But it was music made by young people for young people. By the fall of 1965, DiMucci was 26 and Darin 29, both married men, and the pop world had shifted under their feet. Bob Dylan, Ray Charles and the Beatles had transformed the possibilities of a hit single. They were young adults making music for young adults. DiMucci and Dion were part of that demographic and wanted in on the action.

Their handlers had different ideas. The new-school executives wanted them to stick to the early rock ‘n’ roll style that had made the singers famous. The old-school execs, by contrast, had never believed the first wave of rock music was going to last, and they had the same doubts about this second wave. They believed that the key to a long career was supper clubs, where attractive, tuxedoed men (and attractive, begowned women) crooned the American Songbook—as Frank Sinatra, Tony Bennett and Peggy Lee had.

“Rock ‘n’ roll didn’t exist before we came along,” the 84-year-old DiMucci says over the phone from his current home in Boca Raton, Florida, “so we didn’t have models; we were just winging it. We didn’t have mentors; we were taking it a day at a time. For guys like Gene Vincent, Eddie Cochran and Little Richard, there was nothing the business could do with them, because they were from outer space. But Bobby and I were good-looking guys from New York, so they told us to put down the guitars and sing like Sinatra.”

For Darin, that had been the goal all along. As the son of a single mother (a woman he grew up believing was his sister) and one of the poorest kids in the hard-to-get-into Bronx High School of Science, he was eager to prove all the bullies and the doubters wrong. That desperate need to make it went all the way back to 1944, when at age eight he contracted rheumatic fever that damaged his heart valves.

“He overheard the doctor tell his mother that even with good care and good luck, Bobby was not going to live a full life,” his son Dodd Darin says over the phone from his home in Malibu, California. “This was the key to his ruthlessness, his unwillingness to suffer fools gladly. He was always in a hurry to prove himself. If you weren’t a friend, he could seem arrogant. Even if you were a friend, he seemed driven by ambition. When he was younger, he was worried about one thing—when he walked down the street, he wanted people to say, ‘Hey, look, that’s Bobby Darin.’” “Bobby Darin was more mature than most of us, very purposeful,” adds DiMucci, his friend and frequent tourmate. “He was in a hurry. The first time I met him, he said, ‘I’ve got a rheumatic heart and I’m not going to make it out of my 20s. So I need to be a star by the time I’m 25.’ And he did it.”

For Darin, at least, the move to Sinatra-style crooning made business sense. He had the biggest hit of his career in 1959 with an upbeat, brassy, big-band version of Kurt Weill and Bertolt Brecht’s dark satire, “Mack the Knife” from The Threepenny Opera. Darin also scored Top-20 hits with American Songbook tunes by Hoagy Carmichael and Johnny Mercer. Columbia Records filled DiMucci’s albums with similar numbers, but his heart wasn’t in it and none of them clicked as singles.

But playing the music of your parents’ generation is rarely as gratifying as playing the music of your own generation. As these performers were growing into adulthood, how could their music keep pace? If bouncy songs about adolescent dating weren’t satisfying vehicles and swinging songs about middle-class marriages weren’t either, what kind of songs could be? Dylan and Charles suggested another path. If you tapped into the rich vein of Southern working-class music—folk, blues, country, gospel—and updated it for the changing politics and sexuality of your own time, maybe that offered a third alternative. (There’s a reason Taylor Swift would decades later call her own adult/roots album Folklore.) DiMucci was already plugged into roots music. Even when he was singing doo-wop harmonies on Bronx streetcorners, he would entertain his buddies with songs by Hank Williams and Jimmy Reed.

“Paul Simon and I talk about this all the time,” DiMucci explains. “It was easy for Elvis to tap into the blues; it was all around his backyard. But in our backyards, it was Frank Sinatra. My uncles would sing, and their throats would shake with vibrato; it was disgusting. When I heard Hank Williams sing the blues, he bit the end of each word off. It was life-changing. You can tell all kinds of stories and express all kinds of emotion with the blues. It’s the naked cry of the human heart aching to be in communion with God.”

At Columbia Records, DiMucci was saddled with producers such as Mitch Miller and Bob Mersey, who tolerated rock ‘n’ roll but kept trying to steer the singer into “more mature” material with lusher orchestrations. They reached a détente where DiMucci could do one of his songs for every one of theirs that he recorded. This resulted in some very schizophrenic albums. But then one day, the youngster ran into a different kind of Columbia producer, John Hammond, Sr., the man who had signed Count Basie, Bob Dylan and Aretha Franklin to the label.

“I was in the Columbia Studios,” DiMucci recalls, “sitting on a piano stool with Aretha, playing my new song ‘Drip Drop.’ John Hammond came in and said, ‘You know, you’ve got a flair for the blues.’ He took me into his office, where he had walls and walls of albums. He took out Lightnin’ Hopkins, Leroy Carr, and started playing me stuff. That did it. It got into me. He was playing the roots of what I was about, though I didn’t know it. I knew Jimmy Reed, but I didn’t know who influenced him.”

Meanwhile, the chip that Darin had carried on his shoulder ever since growing up in the Bronx’s shabbier neighborhoods and feeling ostracized at his elite high school had inspired a growing interest in politics. He marched in the legendary Civil Rights rally, 1963’s March on Washington. He began listening to the topical songs of Dylan and Charles and longed to do something similar. Later, he would become very close to liberal reformer Bobby Kennedy and campaign for him. “My dad did not come from money,” Dodd Darin points out. “He came from the wrong side of the tracks. He was always an underdog, so he always related to underdogs. How could he keep singing the swinging crooner numbers, whose lyrics were out of touch with the times? How could he do the old songs when the news was full of the Vietnam war, the battle for civil rights and the war on poverty?”

Both men could sense there was something important happening as folk music morphed into folk-rock. Here was a way to move beyond teenage pop into an adult music that wasn’t as stuffy as their parents’ anniversary parties. Here was a way to talk about the rapid changes in politics, romance and culture by marrying older music to newer instruments. Dion and Darin took off their ties and picked up their acoustic guitars.

The first fruit of Darin’s turn left was to hire a young guitarist named Jim McGuinn away from the Chad Mitchell Trio to back him on a folk-music segment in his live shows. Before long, McGuinn founded the Byrds and changed his first name to Roger. Darin followed that up with a pair of folk-rock albums for Atlantic’s Atco Records: 1966’s If I Were a Carpenter and 1967’s Inside Out, both key parts of the recent Darin reissue series. Of the 22 songs on the two LPs, seven were written by Tim Hardin, four by the Lovin’ Spoonful’s John Sebastian and three by Darin himself. And Darin had immediate success on the charts with his new sound: Hardin’s “If I Were a Carpenter,” with its poor-boy-in-love-with-a-rich-girl theme, was a Top-10 pop single, and Sebastian’s “Sittin’ Here Lovin’ You” was a Top-40 hit.

At this point, it’s worth reminding people who Tim Hardin was. The opening night of the original 1969 Woodstock Festival was devoted to acoustic acts who included Richie Havens, Joan Baez, Arlo Guthrie, Melanie and Hardin. Today Hardin is the least remembered of that quintet, but he was by far the best songwriter of the bunch. He wasn’t as good a singer as Havens or Baez, nor as charming as Guthrie and Melanie, but he wrote two-dozen songs that boasted the same kind of whittled-down elegance of language and melody that marked those of Townes Van Zandt.

Unfortunately, Hardin’s drug problems were even worse than Van Zandt’s. He was erratic in concert and soon exasperated record companies. But a song like “If I Were a Carpenter” was not only a pop hit for Darin but also an R&B hit for the Four Tops and a country hit for Johnny Cash & June Carter. It worked in every genre, because it distilled the tension between lovers of different class backgrounds to a simple story as if it had been honed by generations of oral transmission into an anonymous folk song. Instead it was written by a rambling man from Oregon in a Greenwich Village flat.

There were more songs like that, and they’ve been recorded by everyone from Willie Nelson and Neil Young to Fleetwood Mac and Okkervil River. But no one recorded more of them than Darin. The former teen dream and saloon crooner was no folk purist; he gave the songs chamber-pop arrangements executed by jazz musicians and string players. But Darin exercised tasteful restraint and kept Hardin’s verbal wordplay and melodic leaps out front where they belonged. In 1969, Darin repaid Hardin by writing the tune, “Simple Song of Freedom,” which became a hit single for Hardin in Canada.

As early as 1964, DiMucci was releasing classic blues numbers such as Willie Dixon’s “I’m Your Hoochie Coochie Man” and Arthur Crudup’s “Chicago Blues” as singles, but they barely charted and Columbia refused to include them on an album. It didn’t help that DiMucci, like Hardin, was struggling with a heroin habit. When he had finally cleaned up, in the summer of 1968 after Columbia had dropped him, his old label, Laurie Records, gave him the demo of a song by an obscure gospel songwriter named Dick Holler called “Abraham, Martin and John.” Martin Luther King and Bobby Kennedy had just been assassinated, and the lyrics yearned for a time when it was still possible to believe in the idealism of those two—and their predecessors Abraham Lincoln and John F. Kennedy.

DiMucci dialed back Holler’s anthemic arrangement to an understated folk-rock treatment built around his acoustic guitar and wistful vocal. The single struck a chord and was soon a #4 pop hit. Laurie released an album called Dion, which contained the single plus songs by Dylan, Lightnin’ Hopkins, Joni Mitchell and Jimi Hendrix (an eerily acoustic-ballad version of “Purple Haze”). Columbia put out its own album the following year, Wonder Where I’m Bound, finally letting go of Dion’s unreleased folk-rock experiments for the label earlier in the decade: the Tom Paxton title track plus songs by Dylan, Woody Guthrie, Willie Dixon and three by DiMucci himself. Here was DiMucci as a full-blown folk-blues hero. If they’d been released in 1965, when the Byrds’ first album came out, maybe DiMucci’s career might have been very different.

“I loved hanging out with Tim Hardin, Richie Havens and Tom Paxton at the Village Gaslight.” DiMucci remembers. “I loved sitting in on Dylan’s recording sessions at Columbia. I was always interested in the life of the mind, but I never knew you could sing about this stuff. I fell in love with words. Eventually, when everyone leaves you alone, and you’re not doing hit records anymore—because hit records are a narcotic—when you settle, you realize what comes out of you naturally. For me, when I was in my bedroom singing, what comes out of me naturally is the blues. ‘Teenager in a Love’ was a stretch for me; the blues were never a stretch.”

Darin founded a new label, Direction Records, to release two albums filled entirely with his own protest songs: 1968’s Bobby Darin Born Walden Robert Cassotto and 1969’s Commitment. The first title was a reference to his true birth name, and the second to his dedication to his new cause. Unfortunately, the albums were flops—both commercially and artistically. Darin’s compositions were cute and clever, two adjectives that didn’t serve him well in a genre dominated by Dylan, Hardin, Mitchell and Simon. One exception was “Song for a Dollar,” a revealingly personal song about his career problems. Over a push-and-pull rock ‘n’ roll shuffle, he seemed to address himself as he sang, “How many steaks can you chew, boy? How many cars can you drive? And how many moon ‘n June tap tunes can you write before you’re a lie?”

Another exception was “Long Line Rider,” a choppy blues about a real-life scandal over dead prisoners found on an Arkansas prison farm. As a single, it snuck into the top-80 on the Billboard chart, but when Darin tried to sing it on The Jackie Gleason Show, CBS’s producers wouldn’t let him do it. Sticking to his principles, Darin refused to substitute another song, and walked off the show. For his live shows, he replaced his tuxedo with a denim jacket and his toupee with a black cowboy hat. “Bobby and Elvis were genuine friends,” Dodd Darin says. “In 1969-70, Elvis was selling out the International in Vegas, and he would go to see my dad’s shows. Bobby was doing all of his folk material and none of his earlier songs, and the Vegas audience didn’t dig it. The hotel was paying him $40,000 a week, and people were walking out. Elvis went backstage and said, ‘Bobby, do the hits.’”

Darin got the message, and he retooled his show to reflect the various aspects of his career. Live! At the Desert Inn, taken from a 1971 Vegas show, documents a typical set list: “Mack the Knife,” “Splish Splash” and a Beatles medley. Tucked into the show was a three-song folk-music segment, surprisingly understated and effective, including “If I Were a Carpenter,” “Simple Song of Freedom” and Dylan’s “I’ll Be Your Baby Tonight.” Two years later, the singer finally succumbed to his lifelong heart problems.

“I turned 12 four days before he died,” recalls Dodd Darin, who mostly lived with his mother, actress Sandra Dee, after his parents divorced. “I had traveled with him a lot those final years. The time at his trailer in Big Sur was the best. He could be a celebrity in a tuxedo for 90 minutes and love it, but when it was over, he didn’t care about all that bullshit. He could be a regular guy driving me in his Toyota to the library. I believe if he had lived longer, he could have been like Johnny Cash, mixing his older hits with newer songs.”

DiMucci never had another hit after “Abraham, Martin and John,” but unlike Darin, he lived long enough to collaborate with many of the artists he had influenced: Bruce Springsteen, Paul Simon, Lou Reed, Van Morrison and Eric Clapton. When DiMucci entered the Rock and Roll Hall of Fame in 1989, Reed gave the induction speech. His three latest albums have been devoted to duets with guest stars on blues songs, mostly co-written by the host and his sidekick Mike Aquilina. On Girl Friends, released earlier this month, all the guests are female. It’s not a great album but an enjoyable one; the anthemic “American Hero” even offers echoes of “Abraham, Martin and John.” And the octogenarian DiMucci flirts persuasively with his much younger duet partners such as Shemekia Copeland on “Mama Said” and Christine Ohlman on “Sugar Daddy.”

“Yeah,” he says with a chuckle over the phone, “I may be old, but I’ve still got it going on. I know how to write a song, how to sing it and how to ask the guitarist to play something. But when you ask a real artist to contribute to a song, they bring something to it I never would have imagined. I write a song like ‘Sugar Daddy’ and I ask Christine to sing harmony, and she brings something entirely different and that inspires me. Those surprises are the best.”

One can only hope that some of today’s younger stars will follow the lead of DiMucci and Darin and tap into older strains to discover something new, another way of growing up. One can hope that today’s kids will heed the words of Neil Young, one of pop music’s most famous shapeshifters. “I used to be pissed off at Bobby Darin because he changed styles so much,” Young told Rolling Stone in 1988. “Now I look at him and think he was a fucking genius.”