Afroman - Crazy Rap/Colt 45 gets me every time

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https://youtu.be/0rQ8AVwXMzg

[Edited 12/17/21 7:36am]

Bobby Jimmy & The Critters "N.Y. / L.A. Rappers" is the funniest song if you are an old school hiphop head and understand the musings.

I also love this classic from Eddie Murphy, and its not "Party All The Time" its "Boogie In Your Butt"

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https://www.youtube.com/w...7P538K83iU

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I used to rock to Weird Al when I was a kid and I still think of the lyrics to "I Think I'm A Clone Now" a lot

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https://www.youtube.com/w...vFGKHzY_38

[Edited 12/17/21 7:37am]

Cinny said:

Bobby Jimmy & The Critters "N.Y. / L.A. Rappers" is the funniest song if you are an old school hiphop head and understand the musings.

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This was great!!

If the OP was aiming for legit pop songs that are awkward funny, I would nominate "Hush Hush" a "song" by the "Pussycat Dolls" that incorporates I Will Survive for some reason and is just generally uncomfortable pop dance music. They used to play this song daily at a store I worked at and it was like a daily living nightmare.

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https://www.youtube.com/w...HID13xR3Y0

[Edited 12/17/21 7:37am]

Phase3 said:

Particularly one that makes you smile or laugh almost every time you hear it For me it is this one https://youtu.be/3aJvIFK9-xk The way he says "I hear the thunder" and the female singer saying "be my little baby" I love this song but I just find it hilarious

Is that the Ronnie Spector singing Be My Baby in the video?

Still can't believe this beauty married a flake like Phil Spector back in the day.

It's quite a few of them for me but Dancing Man by Brick immediately comes to mind.

I even find the music hilarious.

Both NWA and Parliament's versions of Automobile are pretty damn funny. Another funny P-Funk one is Aqua Boogie.

Freaky Tales by Too Short is extremely funny, raw, misogynistic, crass and vulgar. It still makes me laugh when I listen to it. Cusswords and Dope Fiend Beat are also hilarious.

Other songs I find funny are Bob George and almost anything by Kool Keith, especially the songs on his Sex Style album.

[Edited 12/17/21 15:39pm]

Otis Redding & Carla Thomas ~ Tramp

Al B. Sure! ~ Papes In The End

Weird Al ~ Taco Grande

Loretta Lynn & Conway Twitty ~ You're The Reason Our Children Are Ugly

Loretta Lynn ~ Fist City

Kool Moe Dee ~ Let's Go

Jerry Reed ~ When You're Hot, You're Hot

B-52s ~ Rock Lobster

Mac Davis ~ It's Hard To Be Humble

Oran "Juice" Jones ~ The Rain

Johnny Cash ~ A Boy Named Sue

DJ Jazzy Jeff & The Fresh Prince ~ I Think I Can Beat Mike Tyson

KoolEaze said:

EmmaMcG said:

The first thoughts that came to mind were a bunch of Weird Al songs. Then, I thought of the Denis Leary song "Asshole". Then I thought of Kevin Wilson's "Hey Santa Claus", which I would wholeheartedly recommend. But! The funniest song I've ever heard is by "Rappin'" Rodney Dangerfield and the song is called "No Respect". Check it out; https://m.youtube.com/wat...LGxWPtgodo

:lol:It´s quite funny. Never knew that Rodney Dangerfield did this.

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Not as funny as Too Short though. Yesterday I listened to the three songs I mentioned above because this thread made me think of those songs, and I couldn´t stop laughing. He´s so vulgar beyond belief.

Not really funny funny, but makes you wonder how someone can come up with such lines, especially Freaky Tales and Dope Fiend Beat.

Weird Al is ok but to me it all sounds a bit forced because, well.....it IS a parody. But Too Short is probably serious and really means what he says, which makes his songs even more hilarious.

MickyDolenz said:

Otis Redding & Carla Thomas ~ Tramp

I agree!

EmmaMcG said:

The funniest song I've ever heard is by "Rappin'" Rodney Dangerfield and the song is called "No Respect". Check it out; https://m.youtube.com/wat...LGxWPtgodo

I had this song on my October playlist. It was produced by the guys who did "The Breaks" by Kurtis Blow. "No respect! No respect" between every line is just like "that's the breaks! that's the breaks!"

KoolEaze said: