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The Biggest Comebacks in Music History

The Biggest Comebacks in Music History

Whether it’s in motion pictures, sports, or the media, nothing is more capricious than fame. Frank Sinatra voiced that sentiment in the song “That’s Life,” when he sang, “You’re ridin’ high in April, shot down in May” – though he promised to be “back on top in June.”

For some music artists, it has taken a lot longer than a few months to get back on top. To determine the biggest comebacks in music history, 24/7 Tempo identified the artists with the longest periods of time between singles consequently entering the American Top 40 chart – comprising the top 40 spots on the Billboard Hot 100 popular singles chart

To be considered for our list, an artist’s “comeback song” had to be a new release at the time it entered the chart. Older releases that became popular again years later were not included. Songs on which an artist was prominently featured, though not the headliner, are considered to be one of that artist’s hits if they are listed under the artist’s name by Billboard. (Here are some famous musicians who never topped the Billboard Hot 100.)

In the music industry, it is not uncommon for artists who had a string of hits to suddenly lose an audience – such as British Invasion groups like the Dave Clark Five, because of the whims of the teenage audience. Other artists fell out of favor because tastes change, or they hit a creative roadblock and didn’t produce material that excited the public. 

But some persevered by recreating their image or collaborating with younger performers to regain the spotlight. An example of the latter is country singer Billy Ray Cyrus. He had a solo hit with “Achy Breaky Heart” in 1992, and in 2008, he had a comeback hit with the song, “Ready Set, Don’t Go,” with an assist from his daughter Miley – and was part of another smash hit in 2019 on the remix of “Old Town Road” by Lil Nas X. (Interested in older hits? Here’s the most popular song the year you were born.)

Though not all the artists on the list are well known, you might be surprised at the droughts experienced by some of the more famous performers in their careers.

Source: Michael Ochs Archives / Michael Ochs Archives via Getty Images

65. Peaches & Herb
> Gap between Top 40 hits: 11 years
> Comeback song: Shake Your Groove Thing (1979)
> Prior Top 40 hit: Two Little Kids (1968)
> Career Top 40 hits: 8 songs (66 weeks total)

Source: Dove / Getty Images

64. Peggy Lee
> Gap between Top 40 hits: 11 years
> Comeback song: Is That All There Is (1969)
> Prior Top 40 hit: Fever (1958)
> Career Top 40 hits: 2 songs (17 weeks total)

Source: Keystone / Getty Images

63. Herb Alpert
> Gap between Top 40 hits: 11 years
> Comeback song: Rise (1979)
> Prior Top 40 hit: This Guy’s In Love With You (1968)
> Career Top 40 hits: 19 songs (124 weeks total)

Source: Hulton Archive / Hulton Archive via Getty Images

62. James Brown
> Gap between Top 40 hits: 11 years, 3 months
> Comeback song: Living In America (1986)
> Prior Top 40 hit: Papa Don’t Take No Mess (Part I) (1974)
> Career Top 40 hits: 44 songs (250 weeks total)

Source: Evening Standard / Hulton Archive via Getty Images

61. Lulu
> Gap between Top 40 hits: 11 years, 5 months
> Comeback song: I Could Never Miss You (More Than I Do) (1981)
> Prior Top 40 hit: Oh Me Oh My (I’m A Fool For You Baby) (1970)
> Career Top 40 hits: 4 songs (36 weeks total)

Source: Michael Ochs Archives / Michael Ochs Archives via Getty Images

60. Ben E. King
> Gap between Top 40 hits: 11 years, 6 months
> Comeback song: Supernatural Thing – Part I (1975)
> Prior Top 40 hit: I (Who Have Nothing) (1963)
> Career Top 40 hits: 6 songs (61 weeks total)

Source: Fin Costello / Redferns via Getty Images

59. Yes
> Gap between Top 40 hits: 11 years, 7 months
> Comeback song: Owner Of A Lonely Heart (1983)
> Prior Top 40 hit: Roundabout (1972)
> Career Top 40 hits: 6 songs (43 weeks total)

Source: Michael Ochs Archives / Getty Images

58. Bad Company
> Gap between Top 40 hits: 11 years, 7 months
> Comeback song: If You Needed Somebody (1991)
> Prior Top 40 hit: Rock ‘n’ Roll Fantasy (1979)
> Career Top 40 hits: 9 songs (64 weeks total)

Source: Frazer Harrison / Getty Images Entertainment via Getty Images

57. Tom Jones
> Gap between Top 40 hits: 11 years, 8 months
> Comeback song: Kiss (w/ The Art of Noise) (1988)
> Prior Top 40 hit: Say You’ll Stay Until Tomorrow (1977)
> Career Top 40 hits: 18 songs (142 weeks total)

Source: David Redfern / Redferns via Getty Images

56. Al Green
> Gap between Top 40 hits: 11 years, 11 months
> Comeback song: Put A Little Love In Your Heart (1988)
> Prior Top 40 hit: Keep Me Cryin’ (1976)
> Career Top 40 hits: 14 songs (135 weeks total)

Source: David Redfern / Redferns via Getty Images

55. Gladys Knight And The Pips
> Gap between Top 40 hits: 12 years, 1 month
> Comeback song: Love Overboard (1988)
> Prior Top 40 hit: Part Time Love (1975)
> Career Top 40 hits: 25 songs (214 weeks total)

Source: MJ Kim / Getty Images Entertainment via Getty Images

54. Enya
> Gap between Top 40 hits: 12 years, 4 months
> Comeback song: Only Time (2001)
> Prior Top 40 hit: Orinoco Flow (Sail Away) (1989)
> Career Top 40 hits: 3 songs (55 weeks total)

Source: Samir Hussein / Getty Images

53. Dave Edmunds
> Gap between Top 40 hits: 12 years, 5 months
> Comeback song: Slipping Away (1983)
> Prior Top 40 hit: I Hear You Knocking (1971)
> Career Top 40 hits: 2 songs (10 weeks total)

Source: Reg Burkett / Hulton Archive via Getty Images

52. Cliff Richard
> Gap between Top 40 hits: 12 years, 6 months
> Comeback song: Devil Woman (1976)
> Prior Top 40 hit: It’s All In The Game (1964)
> Career Top 40 hits: 9 songs (83 weeks total)

Source: ACMA2020 / Contributor / Getty Images

51. Gwen Stefani
> Gap between Top 40 hits: 12 years, 7 months
> Comeback song: Nobody But You (w/ Blake Shelton) (2020)
> Prior Top 40 hit: The Sweet Escape (w/ Akon) (2007)
> Career Top 40 hits: 10 songs (184 weeks total)

Source: Alexander Supertramp/Shutterstock

50. Conway Twitty
> Gap between Top 40 hits: 12 years, 7 months
> Comeback song: You’ve Never Been This Far Before (1973)
> Prior Top 40 hit: C’est Si Bon (It’s So Good) (1961)
> Career Top 40 hits: 9 songs (72 weeks total)

Source: Jason Koerner / Getty Images Entertainment via Getty Images

49. Rakim
> Gap between Top 40 hits: 12 years, 8 months
> Comeback song: Addictive (w/ Truth Hurts) (2002)
> Prior Top 40 hit: Friends (w/ Jody Watley & Eric. B) (1989)
> Career Top 40 hits: 2 songs (27 weeks total)

Source: Henry S. Dziekan III / Getty Images

48. Donny Osmond
> Gap between Top 40 hits: 12 years, 8 months
> Comeback song: Soldier Of Love (1989)
> Prior Top 40 hit: C’mon Marianne (1976)
> Career Top 40 hits: 12 songs (105 weeks total)

Source: Public Domain / Wikimedia Commons

47. Jimmy Ruffin
> Gap between Top 40 hits: 12 years, 11 months
> Comeback song: Hold On To My Love (1980)
> Prior Top 40 hit: Gonna Give Her All The Love I’ve Got (1967)
> Career Top 40 hits: 4 songs (34 weeks total)

Source: Dan Kitwood / Getty Images Entertainment via Getty Images

46. Kylie Minogue
> Gap between Top 40 hits: 13 years
> Comeback song: Can’t Get You Out Of My Head (2002)
> Prior Top 40 hit: It’s No Secret (1989)
> Career Top 40 hits: 5 songs (38 weeks total)

Source: Michael Ochs Archives / Getty Images

45. INXS
> Gap between Top 40 hits: 13 years
> Comeback song: Pretty Vegas (2005)
> Prior Top 40 hit: Not Enough Time (1992)
> Career Top 40 hits: 10 songs (100 weeks total)

Source: Pictorial Parade / Archive Photos via Getty Images

44. Sonny Charles And The Checkmates
> Gap between Top 40 hits: 13 years, 6 months
> Comeback song: Put It In A Magazine (1983)
> Prior Top 40 hit: Black Pearl (1969)
> Career Top 40 hits: 2 songs (12 weeks total)

Source: Michael Ochs Archives / Getty Images

43. Jimmy Dean
> Gap between Top 40 hits: 13 years, 7 months
> Comeback song: I.O.U. (1976)
> Prior Top 40 hit: Little Black Book (1962)
> Career Top 40 hits: 7 songs (42 weeks total)

Source: John Pratt / Hulton Archive via Getty Images

42. The Beatles
> Gap between Top 40 hits: 13 years, 7 months
> Comeback song: Free As A Bird (1995)
> Prior Top 40 hit: Got To Get You Into My Life (1976)
> Career Top 40 hits: 50 songs (430 weeks total)

Source: RB / Redferns via Getty Images

41. Eagles
> Gap between Top 40 hits: 13 years, 9 months
> Comeback song: Get Over It (1994)
> Prior Top 40 hit: Seven Bridges Road (1981)
> Career Top 40 hits: 17 songs (168 weeks total)

Source: austinevan / Flickr

40. Murray Head
> Gap between Top 40 hits: 13 years, 9 months
> Comeback song: One Night In Bangkok (1985)
> Prior Top 40 hit: Superstar (w/ the Trinidad Singers) (1971)
> Career Top 40 hits: 2 songs (21 weeks total)

Source: Rebecca Sapp / Getty Images Entertainment via Getty Images

39. Sergio Mendes
> Gap between Top 40 hits: 14 years, 4 months
> Comeback song: Never Gonna Let You Go (1983)
> Prior Top 40 hit: Scarborough Fair (1968)
> Career Top 40 hits: 5 songs (50 weeks total)

Source: Kevin Winter / Getty Images

38. Weird Al Yankovic
> Gap between Top 40 hits: 14 years, 5 months
> Comeback song: White & Nerdy (2006)
> Prior Top 40 hit: Smells Like Nirvana (1992)
> Career Top 40 hits: 4 songs (20 weeks total)

Source: Mark Metcalfe / Getty Images

37. Radiohead
> Gap between Top 40 hits: 14 years, 7 months
> Comeback song: Nudе (2008)
> Prior Top 40 hit: Creep (1993)
> Career Top 40 hits: 2 songs (6 weeks total)

Source: Keystone / Getty Images

36. Meat Loaf
> Gap between Top 40 hits: 14 years, 9 months
> Comeback song: I’d Do Anything For Love (But I Won’t Do That) (1993)
> Prior Top 40 hit: You Took The Words Right Out Of My Mouth (1979)
> Career Top 40 hits: 7 songs (61 weeks total)

Source: Michael Ochs Archives / Getty Images

35. Carly Simon
> Gap between Top 40 hits: 14 years, 10 months
> Comeback song: Son Of A Gun (w/ Janet, Missy Elliott, & P. Diddy) (2001)
> Prior Top 40 hit: Coming Around Again (1986)
> Career Top 40 hits: 13 songs (123 weeks total)

Source: Laura Levine / Corbis Historical via Getty Images

34. Billy Ray Cyrus
> Gap between Top 40 hits: 15 years, 4 months
> Comeback song: Ready, Set, Don’t Go (w/ Miley Cyrus) (2008)
> Prior Top 40 hit: Achy Breaky Heart (1992)
> Career Top 40 hits: 3 songs (67 weeks total)

Source: Gary Gershoff / Archive Photos via Getty Images

33. Kenny Rogers
> Gap between Top 40 hits: 15 years, 5 months
> Comeback song: Buy Me A Rose (w/ Alison Krauss & Billy Dean) (2000)
> Prior Top 40 hit: What About Me? (w/ Kim Carnes & James Ingram) (1984)
> Career Top 40 hits: 25 songs (246 weeks total)

Source: David Redfern / Redferns via Getty Images

32. Alabama
> Gap between Top 40 hits: 16 years
> Comeback song: God Must Have Spent A Little More Time On You (w/ ‘N Sync) (1999)
> Prior Top 40 hit: The Closer You Get (1983)
> Career Top 40 hits: 6 songs (43 weeks total)

Source: Kevin Winter / Getty Images Entertainment via Getty Images

31. Guns N’ Roses
> Gap between Top 40 hits: 16 years, 1 month
> Comeback song: Chinese Democracy (2008)
> Prior Top 40 hit: November Rain (1992)
> Career Top 40 hits: 9 songs (97 weeks total)

Source: Gie Knaeps / Contributor / Getty Images

30. Barry White
> Gap between Top 40 hits: 16 years, 5 months
> Comeback song: Practice What You Preach (1994)
> Prior Top 40 hit: Oh What A Night For Dancing (1978)
> Career Top 40 hits: 11 songs (99 weeks total)

Source: Roger Kisby / Getty Images Entertainment via Getty Images

29. Clipse
> Gap between Top 40 hits: 16 years, 10 months
> Comeback song: Use This Gospel (w/ Kanye West & Kenny G) (2019)
> Prior Top 40 hit: When The Last Time (2002)
> Career Top 40 hits: 3 songs (21 weeks total)

Source: Kevin Winter / Staff / Getty Images

28. Santana
> Gap between Top 40 hits: 16 years, 10 months
> Comeback song: Smooth (w/ Rob Thomas) (1999)
> Prior Top 40 hit: Hold On (1982)
> Career Top 40 hits: 15 songs (228 weeks total)

Source: Michael Ochs Archives / Getty Images

27. Del Shannon
> Gap between Top 40 hits: 16 years, 10 months
> Comeback song: Sea Of Love (1982)
> Prior Top 40 hit: Stranger In Town (1965)
> Career Top 40 hits: 9 songs (62 weeks total)

Source: Rick Diamond / Getty Images

26. David Cassidy
> Gap between Top 40 hits: 17 years, 9 months
> Comeback song: Lyin’ To Myself (1990)
> Prior Top 40 hit: Looking Through The Eyes Of Love (w/ The Partridge Family) (1973)
> Career Top 40 hits: 12 songs (82 weeks total)

Source: Michael Ochs Archives / Michael Ochs Archives via Getty Images

25. New Kids On The Block
> Gap between Top 40 hits: 17 years, 10 months
> Comeback song: Summertime (2008)
> Prior Top 40 hit: Tonight (1990)
> Career Top 40 hits: 10 songs (103 weeks total)

Source: M. McKeown / Hulton Archive via Getty Images

24. Dusty Springfield
> Gap between Top 40 hits: 17 years, 11 months
> Comeback song: What Have I Done To Deserve This? (w/ Pet Shop Boys) (1987)
> Prior Top 40 hit: A Brand New Me (1969)
> Career Top 40 hits: 11 songs (77 weeks total)

Source: Mike Coppola / Getty Images Entertainment via Getty Images

23. Nas
> Gap between Top 40 hits: 18 years
> Comeback song: Sorry Not Sorry (w/ DJ Khaled, Jay-Z, & James Fauntleroy) (2021)
> Prior Top 40 hit: I Can (2003)
> Career Top 40 hits: 8 songs (86 weeks total)

Source: Michael Ochs Archives / Michael Ochs Archives via Getty Images

22. The Monkees
> Gap between Top 40 hits: 18 years
> Comeback song: That Was Then, This Is Now (1986)
> Prior Top 40 hit: D. W. Washburn (1968)
> Career Top 40 hits: 12 songs (91 weeks total)

Source: Eric Koch / Anefo / Wikimedia Commons

21. Ray Charles
> Gap between Top 40 hits: 18 years, 7 months
> Comeback song: I’ll Be Good To You (w/ Quincy Jones & Chaka Khan) (1989)
> Prior Top 40 hit: Don’t Change On Me (1971)
> Career Top 40 hits: 31 songs (191 weeks total)

Source: Michael Ochs Archives / Getty Images

20. Billy Vera
> Gap between Top 40 hits: 18 years, 9 months
> Comeback song: At This Moment (1986)
> Prior Top 40 hit: Country Girl – City Man (w/ Judy Clay) (1968)
> Career Top 40 hits: 2 songs (16 weeks total)

Source: Lioneldecoster / Wikimedia Commons

19. Gary U.S. Bonds
> Gap between Top 40 hits: 18 years, 9 months
> Comeback song: This Little Girl (1981)
> Prior Top 40 hit: Seven Day Weekend (1962)
> Career Top 40 hits: 7 songs (57 weeks total)

Source: P. Shirley / Hulton Archive via Getty Images

18. Johnny Mathis
> Gap between Top 40 hits: 18 years, 11 months
> Comeback song: Friends In Love (w/ Dionne Warwick) (1982)
> Prior Top 40 hit: Every Step Of The Way (1963)
> Career Top 40 hits: 10 songs (67 weeks total)

Source: Michael Putland / Hulton Archive via Getty Images

17. Willie Nelson
> Gap between Top 40 hits: 19 years
> Comeback song: Beer For My Horses (w/ Toby Keith) (2003)
> Prior Top 40 hit: To All The Girls I’ve Loved Before (w/ Julio Iglesias) (1984)
> Career Top 40 hits: 6 songs (61 weeks total)

Source: Theo Wargo / Getty Images Entertainment via Getty Images

16. Kenny G
> Gap between Top 40 hits: 19 years, 10 months
> Comeback song: Use This Gospel (w/ Kanye West and Clipse) (2019)
> Prior Top 40 hit: Auld Lang Syne (2000)
> Career Top 40 hits: 6 songs (45 weeks total)

Source: Getty Images / Getty Images Entertainment via Getty Images

15. Patti LaBelle
> Gap between Top 40 hits: 21 years, 2 months
> Comeback song: New Attitude (1985)
> Prior Top 40 hit: You’ll Never Walk Alone (w/ The Blue Belles) (1964)
> Career Top 40 hits: 5 songs (31 weeks total)

Source: Chris Ware / Hulton Archive via Getty Images

14. The Isley Brothers
> Gap between Top 40 hits: 21 years, 2 months
> Comeback song: Contagious (2001)
> Prior Top 40 hit: Don’t Say Goodnight (It’s Time For Love) (Parts 1 & 2) (1980)
> Career Top 40 hits: 12 songs (105 weeks total)

Source: David Redfern / Redferns via Getty Images

13. Dolly Parton
> Gap between Top 40 hits: 22 years, 2 months
> Comeback song: When I Get Where I’m Going (w/ Brad Paisley) (2006)
> Prior Top 40 hit: Islands In The Stream (w/ Kenny Rogers) (1983)
> Career Top 40 hits: 8 songs (74 weeks total)

Source: Skip Bolen / Getty Images

12. Aaron Neville
> Gap between Top 40 hits: 22 years, 8 months
> Comeback song: Don’t Know Much (w/ Linda Ronstadt) (1989)
> Prior Top 40 hit: Tell It Like It Is (1966)
> Career Top 40 hits: 4 songs (48 weeks total)

Source: David Redfern / Getty Images

11. Roy Orbison
> Gap between Top 40 hits: 22 years, 9 months
> Comeback song: You Got It (1989)
> Prior Top 40 hit: Twinkle Toes (1966)
> Career Top 40 hits: 23 songs (172 weeks total)

Source: Ground Picture/Shutterstock

10. Tammy Wynette
> Gap between Top 40 hits: 23 years
> Comeback song: Justified And Ancient (w/ The KLF) (1992)
> Prior Top 40 hit: Stand By Your Man (1968)
> Career Top 40 hits: 2 songs (21 weeks total)

Source: Rick Diamond / Getty Images Entertainment via Getty Images

9. Jimmy Buffett
> Gap between Top 40 hits: 23 years, 9 months
> Comeback song: It’s Five O’Clock Somewhere (w/ Alan Jackson) (2003)
> Prior Top 40 hit: Fins (1979)
> Career Top 40 hits: 7 songs (59 weeks total)

Source: Kevin Winter / Getty Images

8. Jimmy Cliff
> Gap between Top 40 hits: 23 years, 10 months
> Comeback song: I Can See Clearly Now (1993)
> Prior Top 40 hit: Wonderful World, Beautiful People (1969)
> Career Top 40 hits: 2 songs (21 weeks total)

Source: Sonia Recchia / Getty Images Entertainment via Getty Images

7. Charlie Sexton
> Gap between Top 40 hits: 23 years, 10 months
> Comeback song: Hallelujah (w/ Justin Timberlake & Matt Morris) (2010)
> Prior Top 40 hit: Beat’s So Lonely (1986)
> Career Top 40 hits: 2 songs (11 weeks total)

Source: Junko Kimura / Getty Images Entertainment via Getty Images

6. Mick Jagger
> Gap between Top 40 hits: 24 years, 2 months
> Comeback song: T.H.E (The Hardest Ever) (w/ will.i.am & Jennifer Lopez) (2011)
> Prior Top 40 hit: Let’s Work (1987)
> Career Top 40 hits: 5 songs (24 weeks total)

Source: Steve Morley / Redferns via Getty Images

5. Dobie Gray
> Gap between Top 40 hits: 24 years, 3 months
> Comeback song: Drift Away (w/ Uncle Kracker) (2003)
> Prior Top 40 hit: You Can Do It (1979)
> Career Top 40 hits: 4 songs (52 weeks total)

Source: Jed Jacobsohn / Getty Images Sport via Getty Images

4. Paul McCartney
> Gap between Top 40 hits: 25 years, 6 months
> Comeback song: Only One (w/ Kanye West) (2015)
> Prior Top 40 hit: My Brave Face (1989)
> Career Top 40 hits: 20 songs (205 weeks total)

Source: By ShowBizz The Adult - Remember Snow the Informer? Still making dope music in Canada, CC BY 3.0, https://commons.wikimedia.org/w/index.php?curid=79977037

3. Snow
> Gap between Top 40 hits: 25 years, 9 months
> Comeback song: Con Calma (w/ Daddy Yankee & Katy Perry) (2019)
> Prior Top 40 hit: Girl, I’ve Been Hurt (1993)
> Career Top 40 hits: 3 songs (38 weeks total)

Source: Frazer Harrison / Getty Images

2. Ozzy Osbourne
> Gap between Top 40 hits: 27 years, 5 months
> Comeback song: Take What You Want (w/ Post Malone & Travis Scott) (2019)
> Prior Top 40 hit: Mama, I’m Coming Home (1992)
> Career Top 40 hits: 3 songs (23 weeks total)

Source: Jo Hale / Getty Images

1. David Bowie
> Gap between Top 40 hits: 28 years, 4 months
> Comeback song: Lazarus (2016)
> Prior Top 40 hit: Never Let Me Down (1987)
> Career Top 40 hits: 13 songs (118 weeks total)

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