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.)

Click here to see the biggest comebacks in music history

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.