"Stranded" by Bobby Jimmy come to mind "I lost on Jeopary" - Weird Al "Star Trekking" - unknown Rocket River
Yoda - Weird Al Star Wars Cantina - Jonathan Davis (sounds like Copacabana) Another One Rides The Bus - Weird Al Grandma In The Corner With A Penis In Her Hand - Frogs The Universe Song - Monty Python Star Wars Disco - Meco Asteroid Field/Finale - Meco The Bertha Butt Boogie - Jimmy Castor Bunch
Anything by Flight Of The Conchords. Clips "Up In Smoke" and most other Cheech & Chong. "Born In East LA" was good too.
"Bobby Brown" "Broken Hearts are for Assholes" "Conehead" "Dynamo Hum" "Disco Boy" "Heavenly Bank Account" "Goblin Girl" "In France" "Jewish Princess" The funny Frank Zappa song list could go on forever, so I will leave you with this chorus from "Dirty Love" I'll ignore your cheap aroma, and your little bo peep diploma, I'll just put you in a coma, with some dirty love, that dirty love
"Rockin' the Suburbs" Ben Folds "Underground" Ben Folds Five "In The Garage" Weezer "You're Pitiful" Weird Al "Be My Girl (Sally)" The Police "Pearl Necklace" ZZ Top
A college roommate had a CD by a band called The Flaming Erudites. I have never heard from or about them since but they did a cover of Living on a Prayer called Living on My Hair that was good, but the showstopper was the cover of Lucky Man called Yuppie Man. "He drove white Porsches..."
Dan Bern - "Tiger Woods" ST - "Institutionalized" Dead Milkmen - "Smokin' Banana Peels" Kinky - "Not Making Jews Like Jesus Anymore" Asylum Street Spankers - "Winning the War on Drugs" and about 50 others Various Tenacious D songs Anything by Richard Cheese
"Ballad of a Dog Named Stains" - Red Peters(best chorus ever!) "Gimme That Nutt" - Eazy E "You Don't Love Me Anymore" - "Weird Al" Yankovic
I like Rolf Harris, who does a lot of comedic songs, but I'll give special mention to Court of King Caractacus, Hair Oil on Me Ears, I'll Be Hanged, Jake the Peg, Nick Teen and Al K. Hall, and Someone's Pinched My Winkles. Also, by Barenaked Ladies: Alcohol, If I Had $1,000,000, and The King of Bedside Manor.
Tiger Woods by Dan Bern is definitely good. also, too many Weird Al songs to mention, but "The Night Santa Went Crazy," "Dare to be Stupid," "It's All About the Pentiums," "White and Nerdy," and "Your Horoscope for Today" come to mind.