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What band or musician makes you laugh like no other? Doesn't have to be novelty Dr. Demento (Weird Al, Adam Sandler,"Fish Heads,""SSSSHaving Cream") stuff. For me it's Stew/the Negro Problem, Randy Newman, Ween and the Bloodhound Gang. The Dandy Warhols and Ani Difranco can be pretty witty at times as well. Nina Hagan and Shirley Bassy have some really weird voices that sometimes crack me up.
Artists with funny lyrics in at least some of their songs: Bob Dylan, Nick Cave (also as a novelist), Randy Newman, Cat Stevens, Tom Waits, David Bowie and Tom Lehrer. Altough actually, humor isn't very important for me when listening to music.
Ray Davies is very witty in many Kinks songs, particularly "A Well Respected Man," "Skin and Bone," and "All of My Friends Were There."
I think Joni Mitchell is funny, sarcastic, honest, witty and ultimately sweet in some of her songs in Court & Spark.
With its emphasis on wordplay, there's lots of humor in hip-hop, and it comes in many different varieties - the did-he-say-that shock comedy of Eminem, the often-hilarious braggadocio of Kanye West, the sheer weirdness of folks like Kool Keith or MF Doom. The Beastie Boys alone have displayed all of these over the course of their career.
Early Beck frequently makes me laugh out loud.
John Grant's Queen of Denmark is filled with anger and pain, but those emotions are often filtered through an off-kilter wit that can catch you off guard (from the title track: "You tell me that my life is based upon a lie/I casually mention that I pissed in your coffee").
Yeah, Queen of Denmark definitely cracked me up a few times; "Jesus Hates Faggots" elicits a grin just for the title. Dylan also frequently makes me laugh, "Talkin' Bear Mountain Picnic Massacre Blues" being a good example. One of the 'novelty acts' I love is Flight of the Conchords; "Mutha'uckas", "Hiphopopotamus", "Robots", the list goes on.
Hamell On Trial would be my pick- his live show is an excellent mix of rock and black comedy.
Pavement, Pixies, Talking Heads all had humor. Bob Dylan of course, The Rolling Stones, The Violent Femmes.
I think The Smiths are underrated for their humor. Their last two albums are chalk full of humor. Only Meat is Murder really lives upto their reputation as a morose and dour band.
The Hold Steady can be witty and amusing. Das Racist has made me laugh.
Bowie's got some funny ones, and "Lola" from the Kinks.
George Clinton has always had a good sense of humor. Same with Paul Westerberg of the Replacements and Jello Biafra of the Dead Kennedeys. Ice Cube, Eazy E, Ol' Dirty Bastard...
Beastie Boys & early Beck are 2 of my favorites some one already mentioned.
The Mothers of Invention - We're Only in It for the Money
I forgot to mention Jarvis from Pulp. Incredibly witty even on his solo records. Art Brut are another band that tickles the funny bone.
Definitely Dylan and the Kinks. Tom Waits can have some pretty silly lyrics when he wants to. Neil Young, "PIECE...OF...CRAP!!".
The Drive By Truckers, definitely. They might be the best lyricists of the decade.
Randy Newman comes off as a little smug to me.
Flight of the Concords is amusing. "Kids are killing each other...with knives and forks! And calling each other things like dork!"