Frank Sinatra was a great singer of course, but he’s also been called a great “interpreter” of famous songs. So much so that when he covered well known songs, he often made or demanded some notable changes to the lyrics.

“Have Yourself a Merry Little Christmas”

The holiday standard debuted in the 1944 movie musical Meet Me in St. Louis. That film was based in and around the 1904 St. Louis World’s Fair, but because of when the song came out—and its painful lyrics about being apart from loved ones for the holidays—closely associates the tune with World War II. Judy Garland’s take from Meet Me in St. Louis included the line “until then we’ll have to muddle through somehow.” When Sinatra covered the song for his 1957 album A Jolly Christmas, he thought that line in particular made the song too somber, so he asked the original song’s co-writer Hugh Martin to “jolly up” the song. Martin’s solution: Out went the line about muddling and in came “Hang a shining star upon the highest bough.”

“High Hopes”

This was one of the most successful songs of Sinatra’s career. Ol’ Blue Eyes sang it in the 1959 movie A Hole in the Head, and it won the Academy Award for Best Original song. Lots of other crooners covered “High Hopes,” such as Sammy Davis Jr., Bing Crosby…and Frank Sinatra himself. Just a year after the initial release of “High Hopes,” Sinatra re-recorded the song with new lyrics about John F. Kennedy, his preferred candidate in the 1960 presidential race. The song became JFK’s official campaign theme song.

“Something”

Sinatra didn’t care much for the rock n’ roll music that threatened his dominance of pop music—with the Beatles’ “Something ” being a notable exception. He once called it “the greatest love song of the past 50 years” and he recorded versions of the George Harrison-written tune in 1970 and 1980. Sinatra only added in a few new lyrics, such as a very Sinatra-esque “You stick around, Jack!” in the middle of the song. In the ’90s, Harrison himself inserted “You stick around, Jack!” when he performed the song live.

“Mrs. Robinson”

Sinatra added in a whole new swingin’ stanza when he recorded a version of Simon and Garfunkel’s 1967 classic from the movie The Graduate. It went a little something like this:
“The PTA, Mrs. Robinson / won’t approve the way you your thing / ding ding ding! / And you’ll get yours, Mrs. Robinson / Foolin’ with that young stuff like you do / boo hoo hoo”