For me the reigning champion is, and I can almost not fathom it ever being upended,
It has everything for hysterically bad unintentional camp: the child’s wavering voice, the out-of-nowhere electric guitar cut-in, the way overly earnest message, and the first time I heard it’s penultimate lines…
*But please don’t tell my daddy…
but my mommy hits me too…*
I thought I was going to choke to death.
May I present Teddy Bear by Red Sovine (not to be confused with the Elvis song of the same name).
It’s supposed to be the touching story of a big-hearted truck driver helping to make a little boy’s dream come true… but instead it’s just, well, creepy.
And, yes, unintentionally hilarious!
The musical Chess is really dated when you look at footage from the original stage production (it’s really cheesy), but what’s so funny about that line?
“The Final Countdown” by Europe. It’s been overused in recent years since Arrested Development showed the world how pompous and ridiculous it is, but it’s really a piece of work.
Burn in Hell!
Valete,
Vox Imperatoris
Hey!* Although they have a good many songs that are much better, that’s just a hilarious song.
Valete,
Vox Imperatoris
*owner of both Aqua albums
http://whiskeyclone.net/ghost/songinfo.php?songID=662
I’m so glad. It was the worst song ever.
Ok hate me if you must, but -
There’s No-One Quite Like Grandma
And a really, really special mention for -
Gang Bang
And finally, one I had hoped to never hear again, ever -
Orville
He’s very missed.
You win the thread.
re: “Barbie Girl” by Aqua:
You forgot this Aqua song. I love the way she pronounces the word “violets” as “wiolets”
“One Night in Bangkok” has been mentioned here, but there is actually an even more hilariously bad song, known only locally I think, but it’s partly in English and partly in Thai. I THINK the title is “Tom, Tom, Where You Go Tonight?” At least that’s the main refrain. The singer has a nasty, gravelly voice, and the song goes something like: “Tom, Tom, where you go tonight? I love Thai girls, I love Patpong.” Quite a catchy tune, too. Patpong is the most famous of our several red-light areas, and it’s about Tom, a farang (Westerner) who goes there.
This song was wildly popular here in the late 1980s, and especially at that time whenever a song was popular, it stayed popular for months on end. Every single farang back then who was walking down the street, including myself, could be sure of suddenly hearing some witty Thai, upon seeing him, call out: “Tom, Tom, where you go tonight?” Followed by peals of raucous laughter as the Thai collapsed in mirth over his own cleverness. This went on for-fucking-ever.
I came in to name this song. Although it really doesn’t fit the criteria, there is a 50-50 chance you will actually cry with laughter listening to it. It’s on my iPod, and I get requests for it from co-workers.
I am normally not so dictatorial, but I must insist that you pause from what you are doing and listen to this song. 
And in the NSFW category, we have this offering from Gunther. Guaranteed to give me a bad case of the giggles whenever I try to listen to it!
I repeat, this video is definitely NSFW!! (I once forgot to include this little warning with a link–not going to make that mistake again!)
It’s social satire, so one could argue that it is supposed to be funny. But it’s not “funny but the artist has no idea that we would think it funny” funny. It’s a critique of shallow people.
Vanilla: No Way No way
I win.
Could be Kung Fu Fighting
but then Lucy in the Sky with Diamondsspoken by Kirk, I mean William Shatner.
No wait worse yet was …
The Ballad of Bilbo Baggins sung by Spock, I mean Leonard Nimoy.
I don’t know how successful they are, but everything I’ve heard from Fall Out Boy is hilariously bad. Exhibit A, a video where an attempt is made to figure out what the hell they’re saying in the song:
http://www.funlol.com/8159/Fall_Out_Boy_Song!.html (slighty NSFW in a cartoony way)
I don’t know how popular it ever became, but me and my wife were watching Scarface the other dayy when they do this montage and the song Take it to the Limit is playing. It struck both of us as being incredibly corny and hilarious.
I have a confession to make. Though I can’t stand Fall Out Boy’s music, Pete Wentz makes me hot. Damn emo boys…