Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years.
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years
Cher - “All I Really Want To Do” (1965) and “Gimme! Gimme! Gimme! (A Man After Midnight)” (2018): 53 years
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years
Cher - “All I Really Want To Do” (1965) and “Gimme! Gimme! Gimme! (A Man After Midnight)” (2018): 53 years
Barbra Streisand - “People” (1964) and “Night of My Life” (2005): 41 years
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years
Cher - “All I Really Want To Do” (1965) and “Gimme! Gimme! Gimme! (A Man After Midnight)” (2018): 53 years
Barbra Streisand - “People” (1964) and “Night of My Life” (2005): 41 years
Debbie Gibson - “Electric Youth” (1987) and “Girls Night Out” (2020): 33 years
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years
Cher - “All I Really Want To Do” (1965) and “Gimme! Gimme! Gimme! (A Man After Midnight)” (2018): 53 years
Barbra Streisand - “People” (1964) and “Night of My Life” (2005): 41 years
Debbie Gibson - “Electric Youth” (1987) and “Girls Night Out” (2020): 33 years
Roy Orbison - “Only the Lonely” (1960) and “You Got It” (1989)
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years
Cher - “All I Really Want To Do” (1965) and “Gimme! Gimme! Gimme! (A Man After Midnight)” (2018): 53 years
Barbra Streisand - “People” (1964) and “Night of My Life” (2005): 41 years
Debbie Gibson - “Electric Youth” (1987) and “Girls Night Out” (2020): 33 years
Roy Orbison - “Only the Lonely” (1960) and “You Got It” (1989): 29 years
Frank Sinatra - “It’s Funny To Everyone But Me” (1939) and “Theme From New York, New York” (1980): 41 years
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years
Cher - “All I Really Want To Do” (1965) and “Gimme! Gimme! Gimme! (A Man After Midnight)” (2018): 53 years
Barbra Streisand - “People” (1964) and “Night of My Life” (2005): 41 years
Debbie Gibson - “Electric Youth” (1987) and “Girls Night Out” (2020): 33 years
Roy Orbison - “Only the Lonely” (1960) and “You Got It” (1989): 29 years
Frank Sinatra - “It’s Funny To Everyone But Me” (1939) and “Theme From New York, New York” (1980): 41 years
Willie Nelson - “No Place For Me” (1957) and “Vote 'Em Out” (2019): 62 years
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years
Cher - “All I Really Want To Do” (1965) and “Gimme! Gimme! Gimme! (A Man After Midnight)” (2018): 53 years
Barbra Streisand - “People” (1964) and “Night of My Life” (2005): 41 years
Debbie Gibson - “Electric Youth” (1987) and “Girls Night Out” (2020): 33 years
Roy Orbison - “Only the Lonely” (1960) and “You Got It” (1989): 29 years
Frank Sinatra - “It’s Funny To Everyone But Me” (1939) and “Theme From New York, New York” (1980): 41 years
Willie Nelson - “No Place For Me” (1957) and “Vote 'Em Out” (2019): 62 years
Conway Twitty - “It’s Only Make Believe” (1958) and “She’s Got a Single Thing in Mind” (1989): 31 years
Singers (not groups or bands) who charted songs at least 25 years apart. If a song is a duet, that’s okay. Any chart (pop; top-40; Billboard; country, etc.) acceptable.
Billy Joe Royal - “Down in the Boondocks” (1965) and “If the Jukebox Took Teardrops” (1991): 26 years.
Johnny Cash - “Come In Stranger” (1958) and “Hurt” (2003): 45 years
Cher - “All I Really Want To Do” (1965) and “Gimme! Gimme! Gimme! (A Man After Midnight)” (2018): 53 years
Barbra Streisand - “People” (1964) and “Night of My Life” (2005): 41 years
Debbie Gibson - “Electric Youth” (1987) and “Girls Night Out” (2020): 33 years
Roy Orbison - “Only the Lonely” (1960) and “You Got It” (1989): 29 years
Frank Sinatra - “It’s Funny To Everyone But Me” (1939) and “Theme From New York, New York” (1980): 41 years
Willie Nelson - “No Place For Me” (1957) and “Vote 'Em Out” (2019): 62 years
Conway Twitty - “It’s Only Make Believe” (1958) and “She’s Got a Single Thing in Mind” (1989): 31 years
Aretha Franklin - “Respect” (1967) and “A Rose Is Still a Rose” (1998): 31 years