Neil Sedaka’s Biggest Billboard Hot 100 Hits: ‘Breaking Up Is Hard to Do’ & Beyond

“I have a theory that there are three kinds of songwriting,” Neil Sedaka posited to Billboard in 2010.

“The emotional is when you go through some trauma and get it out on the page,” he mused. “The intellectual writing is when you have a tune in your head spinning around for many years and you almost rewrite it. And the last is spiritual writing, which is something that comes from a higher power that kind of writes itself and you’re channeling. It’s my theory, but I find that over the years, these are the three types of writing.”

During his lifetime, Sedaka, who died Feb. 27 in Los Angeles at age 86, translated his craft into beloved Billboard chart hits, including three No. 1s among nine top 10s as a recording artist on the Billboard Hot 100. He totaled 30 entries on the chart overall as a singer, from 1958 to 1980, 26 of which he co-wrote, the bulk with writing partner Howard Greenfield (who passed in 1986). Sedaka co-penned all of his top 10s.

Sedaka additionally crowned the Hot 100 as the co-writer, with Greenfield, of Captain & Tenille’s debut smash, “Love Will Keep Us Together,” for four weeks in 1975. (Sedaka had first recorded the song in 1973; the duo’s version famously shouts him out near its close.)

Sedaka initially appeared on the Hot 100 in December 1958 with “The Diary” and first reached the top 10 the following December with “Oh! Carol.” He claimed his first No. 1 with “Breaking Up Is Hard To Do,” for two weeks in June-July 1960. He and Greenfield co-authored all three songs.

The Brooklyn-born entertainer tallied his first 20 Hot 100 hits, all on RCA Victor, through 1966. Sedaka returned in 1974, on Rocket Records — which Elton John had co-founded the year before — with “Bad Blood.” The song led for a week in February 1975. He reigned again for three weeks that October with “Bad Blood,” which includes John on backing vocals. He co-wrote both tracks with Phil Cody.

Sedaka last reached the Hot 100’s top 10 with a slowed-down interpretation of “Breaking Up Is Hard To Do,” which hit No. 8 in 1976.

Sedaka charted his last Hot 100 title with the Elektra Records single “Should’ve Never Let You Go” — a duet with his daughter, Dara. It rose to No. 19 in 1980.

In his 2010 Billboard Q&A, Sedaka shared his belief that a tenet of creating hit songs is to “write something that’s not predictable, something that has turns and twists. Simple is the hardest to write, but if you have a surprise in the song lyrically or melodically, you’re ahead of the game.”

In honor of Sedaka’s chart legacy, below is a recap of his 10 biggest Hot 100 hits.

Neil Sedaka’s Biggest Billboard Hot 100 hits chart is based on actual performance on the weekly Billboard Hot 100, through the Feb. 28, 2026, ranking. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. Due to changes in chart methodology over the years, eras are weighted to account for different chart turnover rates over various periods.