It’s nice to see that the YouTube age has brought back the idea of comedy through song. In the early 70s you had the Smothers Brothers. The late 70s had Steve Martin. The 80s ushered in Spinal Tap and ‘Weird Al’ Yankovic (both of whom continue to record today). But the 90s was a dry spell for comedy set to a tune.
Then sometime in the past decade, YouTube made it possible for funny songs to go viral, and we got an explosion of them — from the political satire of the Jib Jab songs to ‘Dick in a Box’ and a whole lot in between. Adam Sandberg has just about single-handedly carried the torch with ‘Box’ and such gems as ‘Lazy Sunday,’ ‘Natalie Raps’ and ‘Motherlover.’
One of the most popular and amusing viral sensations was this clip by Sarah Silverman, presented to her then-boyfriend Jimmy Kimmel on his show. Silverman is at her cutesy deadpan best here, but it’s Matt Damon who really makes this work. It’s so deliriously wrong in the best possible way.
Kimmel, of course, fought back with his own song, ‘I’m Fucking Ben Affleck,’ also well worth your time.
Meet Me In Montauk 
Ha! Not what I expected to follow Rufus Wainwright week, but okay. Yes, this song is hilarious. I also enjoy trying to pick out the various Miami landmarks in the background (“that’s got to be the Delano, right?”) I love what a great group of good sports that whole Ocean’s Eleven crew and friends appear to be. I’m sure there have always been similar things going on in Hollywood, the Internet just makes it much easier to for them to share their good sense of humor with the rest of the world.
A great song to be sure, made a bit bittersweet by their breakup. I thought they really were a cute couple.
This just makes me laugh every time. I agree Mat Damon steals the show.