I'm not usually a fan of "jazzing up" rock and pop songs, at least not in the sense of playing them with a swing beat and jazz harmonies. But The Beatles classic "When I'm Sixty-Four" works well like this, probably because Paul McCartney wrote in in this style!
Even though the song wasn't recorded until 1967, for their Sgt. Pepper album, the Beatles had played the song in their pre-fame days at the Cavern Club. Paul McCartney had composed the song when he was only 16 years old (can you imagine that kind of talent?!!!) and the group would perform it on those occasions when the power went out at the club. (Presumably on acoustic guitar.) When they began recording Sgt. Pepper a few years later, Paul's father had recently celebrated his 64th birthday, which may have led Paul to revisit the song and record it.
McCartney grew up in a household where the jazzy songs of the 1920s-1940s were heard in family singalongs around the piano, and he was very much influenced by their melodies, chords, and rhythms. All of these elements made their way into When I;m Sixty-Four, which sounds as though it could have been written decades earlier. This is one reason why the song works so well in a stride style. I've simply taken the swing "2-beat" bass line that McCartney uses and incorporated it into a fuller left hand stride pattern.
You can watch and listen to me play it here:
When I'm Sixty-Four: Complete Beatles Piano #16
It's nice when we encounter a pop song that lends itself to stride piano so naturally. Try it yourself!
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