5. Roy Orbison
> Comeback song: You Got It
> Entered Top 40: 2/18/1989
> Years between Top 40 hits: 22.7
Roy Orbison found tremendous success in the early 1960s, during which he landed nine singles in Billboard’s Top 10. He would achieve one final hit with “You Got It,” released in 1989, almost 23 years after his previous Top 40 song “Twinkle Toes.” Unfortunately, Orbison died of a heart attack about two months before the release of the song, at the age of 52.
4. Jimmy Cliff
> Comeback song: I Can See Clearly Now
> Entered Top 40: 12/4/1993
> Years between Top 40 hits: 23.8
Reggae artist Jimmy Cliff scored a couple of crossover hits on the Hot 100 in 1970 with “Come Into My Life” and “Wonderful World, Beautiful People.” It would take almost 24 years for him to return with “I Can See Clearly Now,” a Johnny Nash song that Cliff covered for the movie “Cool Runnings.”
3. Aaron Neville
> Comeback song: Everybody Plays The Fool
> Entered Top 40: 8/24/1991
> Years between Top 40 hits: 24.5
Silk-throated Aaron Neville went nearly a quarter of a century between Top 40 hits. Neville, out of the fertile music scene in New Orleans, returned to the Top 40 in 1991 with the song “Everybody Plays The Fool.” His previous Top 40 effort had been “Tell It Like It Is,” which reached No. 2 on the Billboard Hot 100 chart in 1967.
2. David Bowie
> Comeback song: Lazarus
> Entered Top 40: 1/30/2016
> Years between Top 40 hits: 28.4
Though David Bowie had a minor hit with “I’m Afraid of Americans” in 1997, he had a long Top 40 dry spell following the release of “Never Let Me Down” in 1987. He reached No. 40 on the Hot 100 once again with “Lazarus” on Jan. 30, 2016. Sadly, the song reached the chart just over one week after Bowie’s death at age 69.
1. Paul McCartney
> Comeback song: FourFiveSeconds (with Rihanna and Kanye West)
> Entered Top 40: 2/14/2015
> Years between Top 40 hits: 29.1
Despite his unparalleled success as a member of The Beatles and Wings, Paul McCartney had two prolonged breaks between Top 40 hits. First, his song “Take It Away” became a Top 40 hit more than 11 years after “Another Day” — the first single he released after The Beatles broke up — landed on the Top 40 in 1971. Then, more than 29 years after his single “Spies Like Us” broke into the Top 40, McCartney returned with the 2015 collaborative effort “FourFiveSeconds,” on which he performed alongside Rihanna and Kanye West.