The Frank Sinatra cover Paul Simon hated with a passion- He can't do that

(Credits: Far Out / Joost Evers. Nationaal Archief / Capitol Records)

Mon 3 November 2025 19:00, UK

As a millennial, learning to love 1960s music was a tricky task.

Because before I could scratch together the coins to start buying my own records, the places I would first hear these songs would be films. And at the turn of the millennium, there was a string of trashy movies that celebrated the music of this decade with what I now realise were horrific pop-punk covers.  

Before I ever heard Simon and Garfunkel sing ‘Mrs Robinson’ for the first time, and before I ever experienced the beautiful realisation that this song was part of a curated soundtrack for The Graduate, it was forced upon me through the lens of ultimate millennial trash. When one of the most famed characters of that era – Stifler’s Mom – was seduced by Paul Finch in American Pie, the great Simon and Garfunkel track rang out.

Granted, given the subject matter, it was perhaps the perfect song to use in that film. But then, 13 years later, when I had watched The Graduate, and learned to love Paul Simon’s music, and then subsequently heard The Lemonheads’ god awful cover of the song in The Wolf of Wall Street, I wondered how and why this track had become a pawn in cultural exploitation? Especially when its origin is related to such a hyper-specific cinematic moment.

Well, it’s likely because the 1960s as a decade were rife with covers. It was commonplace for artists to launch their careers and achieve chart number ones by reimagining the work of another artist. But, in 1969, the year in which Frank Sinatra decided to cover it, you could safely say that the iconic musician needed neither a career launch nor a chart number one.

But he covered the track anyway and did it in true Sinatra big band style, but with completely different lyrics. Not only had the words changed, but it was a far cry from the humble beginnings of Simon and Garfunkel, and Simon wasn’t pleased.

“I met him once. It was very interesting, too, because he made a cover record of my song ‘Mrs Robinson,’” Simon told Stephen Colbert. “And he changed the lyrics.”

He continued, “The original lyrics were fantastic. But when I first heard Sinatra’s, it was like, ‘Man, ring a ding, ding you Mrs Robinson. Jesus loves you more,’ and this is in the ’60s, and I said, ‘He can’t do that,’” Simon continued.

Simon explained how a Warner Bros producer had taken the blame for the lyric change, removing Sinatra from any blame. Sinatra later told Simon that he was actually adamant on pausing the release of the song, but Simon openly admitted, “You can’t stop a Frank record.”

He concluded, “And then later, I fell in love with that record. And when you play music after the concert is over, that’s the first song.”

Sinatra’s weight as a cultural titan surely had some impact in swaying Simon’s stance. However, its use in a lewd underage sex movie still hasn’t made the great for Simon, while there has been no amendment on his scornful conclusion of The Lemonheads’ cover.

Related Topics