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Top Five Comedy Songs

With The Lonely Island’s  The Wack Album being released last month, I figured I’d go ahead and make a list of my five favorite tracks by comedy musicians. Just as a disclaimer though, I decided to place the limit of one song per artist for the sake of diversity and kept it as clean as possible.


5. Gimme Some Money - Spinal Tap

    This was the second single released by the fictional group and sees them imitate most of the quintessential British Invasion groups of the 60s before getting all psychadelic. The premise involves lead singer David St. Hubbins asking his girlfriend to help him out and hook him up with some extra cash. The best part is when he gets desperate and begins to insult her as he sings “Your face is okay / but your purse is too tight / I’m looking for pound notes, loose change, bad checks, anything”

4. Amish Paradise - Weird Al Yankovic

    This song sees Weird Al parodying Coolio’s hit “Gangsta’s Paradise,” probably the only redeeming aspect of the Michelle Pfeiffer vehicle that was Dangerous Minds. Interestingly enough, that song in itself is a reworking of the Stevie Wonder song “Pastime Paradise,” turning a complaint on materialism into an atonement for a violent lifestyle fueled by just that sort of greed. But, instead of a regretful lament, the comedian turns his version into a prideful brag about how easy and worthwhile simple lifestyle is, bringing everything full circle.

3. Idiot Boyfriend - Jimmy Fallon

    One of the current talk show host’s first forays into comedic songwriting occurred over ten years ago when he was still on SNL. Because it doesn’t rely on extra star power like most of his songs on the grammy-winning Blow Your Pants Off, this cut off of The Bathroom Wall is set above the rest. The song is basically a confession to his significant other that he’s essentially a moron and is inevitably bound to screw everything up despite the fact that he means well. The fact that it’s in the style of 1970s disco and he uses a falsetto the whole time makes it even more hilarious. The best part is when he breaks it down to talk about his plans to get romantic back at his parents house and asks, “Hey, baby, you like fine cooking? ‘Cause you know what? I got a Swanson’s dinner in the freezer with your name on it!” He then proceeds to ask her to mimic sex sounds.

2. Bowie - Flight of the Conchords

    With this track, the folk duo does everything they can to make fun of all David Bowie’s eccentricities, and it works perfectly. They mock his songs “Space Oddity” “John, I’m Only Dancing,” “Let’s Dance,” and “Sound and Vision” and even reference “Changes” and “Life on Mars” at certain points. Probably my favorite quote from the song has got to be at the beginning when Jemaine Clement uses his perfect Bowie impression to introduce this exchange: “Does the space cold make your nipples go pointy, Bowie? Do you use your pointy nipples as telescopic antennae to transmit data back to Earth?” I bet he does too.

1. Natalie’s Rap - The Lonely Island

     I guess it’s only fitting that I give the top spot to the group that inspired this article. This is probably the least known and/or remembered Lonely Island track. It was one of the earliest SNL Digital Shorts and came out mere weeks before the movie based on Alan Moore’s V for Vendetta came out, probably best remembered for where Natalie Portman shaves her head. I would have to assume that’s what inspired a rap about how much of an uninhibited, badass Natalie Portman is when she was publicly perceived as the cute, sweet-hearted Harvard grad. But, quite frankly, the dichotomy of that notion is enough of an inspiration as it is. I dare you not to crack up.

Director of Digital | Radio Milwaukee