“Some years I’m the coolest thing that ever happened, and then the next year everyone’s so over me,” Cher told Rolling Stone in 1999. She had just released “Believe,” which set the record for longest gap between Number Ones on Billboard’s Hot 100, a milestone that stands to this day. She joins many other big names — from the Beach Boys to Aretha Franklin and Meat Loaf — on our list of artists who mixed up a cocktail of fortitude, talent and luck to fight their way back onto the charts years after they first scored a hit. (Note: Our list measures the time between an artist’s equivalent milestones — Top 10 tracks, Hot 100 appearances and so on — so in some cases, we’ve omitted certain other charting songs that came in between.)
The songs: “Spies Like Us” (1986, Number Seven), “FourFiveSeconds” (2015, Number Four)
Years between hits: 29
No, the Paul McCartney and Wings title track for the Chevy Chase-Dan Aykroyd vehicle Spies Like Us probably didn’t place high on the list of reasons for his knighthood. Perhaps the most noteworthy thing about the forgettable cut is that the BBC wouldn’t air the music video because, at the time, British labor laws prevented non-musicians from performing in videos, and Chase and Aykroyd were “playing” instruments.
It’d be hard to argue that McCartney struggled over the course of the years that followed, but it did take a healthy amount of time for him to crack the Top 10, his comfort zone, again. In fact, he set the record for the longest gap between Top 10 hits, at 29 years. He reclaimed a spot in 2015 via, of all things, a heartfelt Rihanna-and-Kanye West tune. It’s less surprising considering his admiration of West. “I love Kanye, and he loves me,” McCartney said in an interview. “He’s a monster, he’s a crazy guy who comes up with great stuff so he inspires me.”
The songs: “Black Magic Woman” (1971, Number Four), “Smooth” (1999, Number One)
Years between hits: 28
After his riveting, super-high Woodstock performance, Carlos Santana set about making a true rock classic: Abraxas. Contained within was a mystical take on Peter Green’s “Black Magic Woman.” As usual here, Santana shied away from the microphone: The song was sung by keyboardist Gregg Rolie. It shot right up the charts.
In the decades between Abraxas and 1999’s Supernatural, Santana and his group made records at a steady clip: It just took, well, a supernatural occurrence for a comeback. “I know it sounds New Age and mumbo-jumbo, but in my meditation, this entity — which is called Methatron — he said, ‘We want to hook you back to the radio-airwave frequency,’” Santana told RS in 1999. “ ‘We want you to reach junior high schools, high schools and universities. Once you reach them — because we are going to connect you with the best artist of the day — then we want you to present them a new menu.’ ” As far as the lead single and chart topper, “Smooth,” is considered, the “best artist of the day” was none other than Matchbox Twenty’s Rob Thomas. Thomas’ laborious singing and the song’s cheesy lyrics haven’t aged well, but Santana’s work on the guitar is always worth a listen. The song also set a record for the longest stretch (30 years) between an artist’s Hot 100 debut entry and a first Number One. Props, Methatron.
The songs: “Oh, Pretty Woman” (1964, Number One), “You Got It” (1989, Number Nine)
Years between hits: 25
“Oh, Pretty Woman” was the last in a long line of hits for Roy Orbison in the 1960s, coming on the heels of classics like “Only the Lonely”, “Running Scared” and “Crying.” But, it was just a matter of time before he, of timeless cool, was rediscovered by another generation. Unfortunately, the Caruso of Rock wasn’t around to see it happen. “You Got It,” which was co-written with his Traveling Wilburys bandmates Tom Petty and Jeff Lynne, hit the charts the month after Orbison died of a heart attack at 52. He gave only one public performance of it in Antwerp, and the footage was used for the music video. The song itself is a marvelous original with no expiration date.
Before Orbison’s demise, he spoke to Rolling Stone for an interview that was published upon the release of Mystery Girl, the album anchored by “You Got It.” “There has been a concerted effort for the career to make sense for the last three years,” Orbison said when asked about his resurgence. He credited Linda Ronstadt, Don McLean and Van Halen covers, the prominent usage of “In Dreams” in the film Blue Velvet and his induction into the Rock and Rock Hall of Fame. “It’s a stupendous undertaking. But great things are stirring, you know? Being someone who was there at the founding of rock & roll, it’s good that at the age I am I’m being accepted and recognized.” Serendipitously, “Oh, Pretty Woman” took on a posthumous life of its own, with a starring role in the 1990 romantic comedy film, Pretty Woman, and a live performance on an HBO special that garnered Orbison a Grammy.
The songs: “Tell It Like It Is” (1967, Number Two), “Don’t Know Much” (1989, Number Two)
Years between hits: 22
Before the Neville Brothers banded together, Aaron was a star of his own, right out of the gate. When he was all of 25 years old, Neville recorded “Tell It Like It Is” in his hometown of New Orleans. The gorgeously sung track quickly became a bestseller, only to come up one spot short of the Monkees’ “I’m a Believer.” The problem was, Par Lo, Neville’s label at the time, went bankrupt. “I never really got paid for ‘Tell It Like Is,’ but I look back at it and say, ‘God knew what he was doing’; he probably figured that if I had got money back in them days I wouldn’t be here now,” Neville said in an interview.“That’s OK. I’m here. And I’m still singing the song.”
He definitely got paid for his number two Number Two. Neville joined forces with Linda Ronstadt for the tear-jerking “Don’t Know Much.” They won a Grammy for their take on the Barry Mann tune that has sold just shy of a million copies.
The songs: “Got to Get You Into My Life” (1976, Number Seven), “Free as a Bird” (1995, Number Six)
Years between hits: 19
The fact that “Got to Get You Into My Life” charted in 1976, six years after the Beatles broke up, is strange. That the song originally appeared a decade prior, on Revolver, is stranger still. The strangest thing of all may be that human beings were alive in 1976 who didn’t already own every Beatles album. Anyhow, the rambunctious, passionate cut is about yearning to score some pot, not a girl. A prime example of the Beatles’ staying power, “Got to Get You” was reintroduced as part of one of the group’s many, many compilations, Rock ’n’ Roll Music.
Ahead of their 1995 Anthology collection, the surviving Beatles wanted to add something special onto the release, and got back together for “Free as a Bird.” Yoko Ono sent Paul McCartney a collection of Lennon demos, one of which was recorded in 1977 at the couple’s New York apartment. Paul McCartney, George Harrison, Ringo Starr and producer Jeff Lynne fleshed the track out at McCartney’s home studio in Sussex, England. The result was the trippy, guitar-heavy “Free as a Bird.” “I think it was George who said, ‘No, we need a producer. It could be dangerous to just all go into the studio, it could get nasty,’” McCartney recalled. Referring to Lennon’s demo, he said, “It was a crackly old thing. Jeff took the cassette tape and put it in time. Jeff is very precise. There’s not a thing wrong.”
The songs: “You Rock My World” (2001, Number 10), “Love Never Felt So Good” (2014, Number Nine)
Years between hits: 13
By 2001, MJ hadn’t had a Top 10 in six years — “You Are Not Alone” was released in ’95 — an eternity for the King of Pop. “You Rock My World,” a throwback number that had all the dance-pop flair of Jackson’s earlier work with Quincy Jones, delivered. Plucked from his final proper studio album, Invincible, it also featured one of the weirder music videos of all time. It’s more than 13 minutes long. Jackson and Chris Tucker play dancing stalkers. Michael Madsen is in it. That mean guy from The Untouchables is in it. Marlon Brando is in it!
Five years after Jackson’s death, a second batch of posthumous songs were released as Xscape. “Love Never Felt So Good” came in two versions: One had MJ going solo, and the other featured another fleet-of-foot singer with an initialed nickname. Jackson’s ebullient vocal track was taken from a 1983 session with Paul Anka, so it’d only be natural to have Justin Timberlake join him on it 31 years later, right? Sure. When executive producer L.A. Reid introduced the song at the iHeartRadio Awards, he said, “When I first went into Michael’s archives and heard the in-the-raw version of the song you’re about to hear, I was instantly reminded that, yes, Michael Jackson is the greatest.” This year, Jackson charted in the Top 10 again, making an appearance on Drake’s “Don’t Matter to Me.” His vocals were taken from that same 1983 Anka session.
The songs: “Two Out of Three Ain’t Bad” (1978, Number 11), “I’d Do Anything for Love (But I Won’t Do That)” (1993, Number One)
Years between hits: 15
Meat Loaf hit the big time with Bat of Hell, his 1977 glam opera written with Jim Steinman and produced by Todd Rundgren. “Two Out of Three Ain’t Bad,” an anthem to compromise in which the lovelorn, baseball players, and parents with a problem child might find succor, almost cracked the Top 10. Not bad.
In the song’s wake, Meat Loaf didn’t fare so well. His record company refused to pay for the Steinman-penned “Total Eclipse of the Heart” and “Making Love Out of Nothing at All,” both of which became hits for other artists. Meat Loaf had to declare bankruptcy. Then, he and Steinman finally finished the sequel they’d been tinkering with since 1978. “I’m different from Bette or Cher or Sinatra,” Meat Loaf told RS in 1993, as Bat Out of Hell II: Back Into Hell, stormed the charts, led by its first single. They had struck platinum again. “This might be a huge ego thing, but I tend to think of myself as the Robert De Niro of rock. I know that’s absurd, but my idols are either sports figures or Robert De Niro.”
The Loaf was speaking from backstage at The Tonight Show, where he was to perform “I’d Do Anything for Love (But I Won’t Do That)” after Richard Gere talked to Jay Leno in one of the most Nineties moments ever committed to print. “When I hear these lyrics, I think they’re the funniest things I’ve ever heard,” Meat Loaf said. The song is as epic as they come: a 12-minute-long power-ballad odyssey in which he trades verses with singer Lorraine Crosby and outlines exactly four things he won’t do, you know, for love. “I play everything for real. That’s the best comedy. And I know I’ll get to do another one, and I know that I’ll always keep working. I’ve always imagined myself ending up being Wilford Brimley in 20 years.” He was right: Bat Out of Hell III: The Monster Is Loose was released in 2006.
The songs: “Wonderland by Night” (1961, Number 15), “4th Dimension” (2018, Number 42)
Years between hits: 57
Louis Prima was a jazz trumpeter and singer who kept popping up in different eras. He released his take on Bert Kaempfert’s “Wonderland by Night” in 1961, and it charted at a respectable Number 15. In 1967, Prima performed the part of King Louie in the animated version of The Jungle Book, where he sang “I Wan’na Be Like You.” In the movie Big Night, everyone is waiting for him to show. That Nineties Gap commercial features his “Jump, Jive an’ Wail.” Brian Setzer shouted him out in a song. And just this year, 40 years after his death, he broke the record for the longest gap between chart entries on Billboard’s Hot 100.
Kanye and Cudi’s album Kids See Ghosts contains the track “4th Dimension.” Adding to the Legend of Prima, he is a featured player. His Christmas jingle “What Will Santa Claus Say (When He Finds Everybody Singin’)” ushers in the tune and does some heavy lifting as a sample. “Either Kanye has an encyclopedic knowledge of music or he has people who are assisting him to find this, but this is not something that comes to the front of my mind, in terms of a Prima song,” Anthony Sylvester, attorney for Prima’s late wife, said in an interview. “When the request was made for a call, I expected it would be something a little more popular. I actually expected somehow he wanted to sample ‘Sing, Sing, Sing’ — maybe the drum part or something. For this one, my jaw dropped.”
The songs: “For Once in My Life” (1967, Number 91), “Body and Soul” (2011, Number 87)
Years between hits: 43
Tony Bennett’s classic rendition of the swing standard “For Once in My Life” charted the year before Stevie Wonder’s did. It was a whopping 43 years later that he made it back onto the Hot 100 with a fresh arrangement of the jazz standard “Body and Soul.” For the latter’s appearance on the charts, all Mr. Bennett had to do was team up with the late Amy Winehouse. The two took to the studio in March 2011, and she died that July, making it her final recording. It also, at the time, made Bennett the oldest person ever to find his way onto the Hot 100. “Jazz is a wonderful art,” he said in an interview that year. “Listening to it, I compare it to watching the greatest tennis player who’s so intelligent about where he places the ball, it becomes effortless. The great ones that are very talented know just how to turn jazz singing into a performance that’s unforgettable. And Amy had that gift. The fact that she died at 27 years old is just horrible to me. If she had lived, she would’ve been right up there with Billie Holiday and Dinah Washington. It’s just a tragedy.”
The songs: “Dark Lady” (1974, Number One), “Believe” (1998, Number One)
Years between hits: 24
If you’ve never heard “Dark Lady” before — or even if it’s been a while — we’d suggest you do it twice. First, as you watch this campy, fabulous video from The Sonny & Cher Comedy Hour and, then, again as you bewilderingly gaze upon a cartoon that’s a step-by-step exposition of the plot of the song. And what a song! No wonder Cher has a show coming to Broadway soon.
It’s hard to believe that Cher is 72 now, just as it’s equally unfathomable that she set a record for the longest time between Number Ones when she released “Believe” in 1998. (The song also made Cher the oldest woman with a Number One and set a record for longest time ever between a first and a last Number One: “I Got You Babe” took the top spot 33 years and 232 days before “Believe” ceded its crown.) The album of the same name is one of her personal favorites and the song, a bona fide club banger with an empowering message, still brings it. When asked by Rolling Stone in 1999 if she actually believed in life after love, Cher replied, “Definitely. I’ve experienced it. It’s been a long time; I’ve never been alone this long.”
The Beach Boys
The songs: “Good Vibrations” (1966, Number One), “Kokomo” (1988, Number One)
Years between hits: 22
“Good Vibrations” is one of the cornerstone classic-rock songs — RS ranked it sixth of all time — and a track that ushered in a new wave of psychedelic experimentation in music. God bless the hip kids of 1966 for sending it to the top of the charts.
The notoriously expensive “Good Vibrations” recording was, of course, spearheaded by a 24-year-old Brian Wilson with the intention of inclusion on the unfinished album Smile. It doesn’t take multiple listens of the trite “Kokomo” to realize he didn’t have a hand in that one. Mike Love, who wrote the lyrics to “Good Vibrations,” helped put together the images of the “Kokomo” fantasy land and said he wished Wilson had been a part of it. Wilson, for his part, liked the song but couldn’t even recognize that it was the Beach Boys. “We tried to get him to record with us on that song,” Love said of Wilson in an interview. “But he was under the spell, some might say, of Dr. [Eugene] Landy, the psychologist who governed his every move.” Love goes on to report that Wilson appeared in the video — he does not. Who does, though? Well, John Stamos on congas, of course — never forget when the Beach Boys were on Full House — and clips of Tom Cruise flipping bottles from the film Cocktail, for which the song was written.
The songs: “Respect” (1967, Number One), “I Knew You Were Waiting (For Me)” (1987, Number One)
Years between hits: 20
Milestone reached again: Number One
The recently departed Queen of Soul had to wait a while to get back on top. “Respect” is, of course, an unstoppable masterpiece: Rolling Stone named it the fifth-best rock song in history. Though Otis Redding wrote the song, it will forever be known as Aretha’s.
By the time she teamed up with George Michael for a duet on “I Knew You Were Waiting (For Me),” Franklin was already a legend. The uplifting song cemented that fact for a new generation, and sold a boatload. “He had a very unique sound, very different from anything that was out there,” Franklin told Entertainment Weekly about Michael, just after his death on Christmas of 2016. “When Clive [Davis] suggested we get together for ‘I Knew You Were Waiting,’ I was all ready. It reminded me of Jerry Wexler. We’d go in the studio and cut songs. If we were happy with what we recorded, Jerry would say, ‘Let’s wait until tomorrow. If we feel the same way [then] that we do now, maybe we have a hit.’ ‘I Knew You Were Waiting’ had that. Musically, it does not grow old.” Wexler produced “Respect,” which also does not grow old.
The songs: “Don’t Go Breaking My Heart” (1976, Number One), “Don’t Let the Sun Go Down on Me” (1992, Number One)
Years between hits: 16
Elton John has scored 58 Billboard Top 40 singles, second only to Elvis. So, yeah, that’s a lot of hits. Still, the 1980s were a bit of a dry spell by his standards. In 1976, he put a cherry on top of a hugely successful decade with the release of a duet with Kiki Dee, “Don’t Go Breaking My Heart.” Sir Elton had originally wanted Dusty Springfield for the female part, but Dee’s upper register proved a fine substitute. “That’s a complete one-off single,” John told Rolling Stone in the same ’76 interview where he came out as bisexual. “I was messing around in the studio one day on the electric piano and came up with the title line. I made a hasty phone call to Barbados and said, ‘Write a duet,’ and [John collaborator Bernie] Taupin nearly died ’cause he’d never done one. It’s very hard anyway.” John has gone on to perform the duet with Miss Piggy, Minnie Mouse and the Spice Girls, among others.
“Don’t Let the Sun Go Down on Me” originally came out in 1974, but the sentimental ballad saw new life when it was released in 1992 as a duet with none other than George Michael. John and Michael were close friends for years, then had a very public feud after the single’s release, but allegedly reconciled before Michael’s death in 2016. Afterward, John honored Michael by performing “Don’t Let the Sun Go Down on Me” at a show in Las Vegas.
The songs: “Give Me Love (Give Me Peace on Earth)” (1973, Number One), “Got My Mind Set on You” (1988, Number One)
Years between hits: 15
All told, the Quiet Beatle had three solo Number Ones. The first was “My Sweet Lord,” in 1970, followed by these two. “Give Me Love (Give Me Peace on Earth)” is a gorgeous, spare anthem with kick-ass slide guitar and spiritual ponderings from George. It also notably dethroned Paul McCartney’s Wings tune “My Love” from atop its perch on the Hot 100, marking the only time two former Beatles held the top two spots in the U.S.
“Got My Mind Set On You” is a total about-face, not immediately recognizable as a George song. That might be because it’s not. It was written by Rudy Clark for James Ray. But, oh, that beat: Harrison’s clap-along version topped the charts in the week leading up to the Beatles’ induction into the Rock and Roll Hall of Fame. (Weird Al later poked fun at the simplistic lyrics with “(This Song’s Just) Six Words Long.”) In an interview with Rolling Stone, upon the release of Cloud Nine, the album from which the single came, Harrison seems to explain why he had transitioned away from his earlier, loftier work. “What’s happened over the years is all these people — Eric Clapton, Bob Dylan, Ringo, whoever I come across of these old guys — we’re not old,” Harrison said. “But you know what I mean — they’re getting better. The older we all get — maybe it’s this mellowing process or whatever — everybody seems to have gotten so much more at ease.”
The songs: “All of Me” (1932, Number One), “Hello, Dolly! (1964, Number One)
Years between hits: 32
Billboard’s Hot 100 chart has been around since 1958. That makes tracking sales figures that predate its foundation something of a fraught enterprise. Yet, according to Joel Whitburn’s Pop Memories 1890–1954: The History of American Popular Music, Louis Armstrong had a Number One single on February 20th, 1932, with the jazz standard “All of Me” — a year after its composition.
And guess what? Satchmo was back 32 years later — an astounding accomplishment by any measurement — with “Hello, Dolly!” What’s more, Armstrong became the oldest artist to ever top the Hot 100 when he was 62-years-and-279-days-awesome. Still not satisfied? His recording of the title track from the musical of the same name ended the Beatles’ streak of three Number Ones in a row over 14 consecutive weeks. The Beatles and Louis on the charts at the same time: What a wonderful world.