* The [[https://www.youtube.com/watch?v=uq-gYOrU8bA music-video version]] of "You Can Call Me Al" he did with Creator/ChevyChase, with Chase being the one "singing" the lyrics while a bored Simon slouches and twiddles his thumbs (the culmination of a RunningGag on ''Series/SaturdayNightLive'' where Chase claimed to be Simon). Bonus points for Chase "setting down" a glass of water on the empty bongo stand, ignoring how it immediately drops through and onto the floor.
* While it's most famous for its goofy chorus ("Just slip out the back, Jack/Make a new plan, Stan") "Fifty Ways to Leave Your Lover" becomes really hilarious when the verses reveal that this blunt advice is coming from a supposedly sophisticated woman manipulating the naive singer into ditching his current love and getting with her:
-->She said, it's really not my habit to intrude
-->And furthermore I hope my meaning won't be lost or misconstrued
-->So I'll repeat myself, at the risk of being crude
-->There must be fifty ways to leave your lover...