Fela Kuti.
- born into an upper-class family in Nigeria, sent to London to study medicine but decided to enroll in music school instead. Then went to LA and hooked up with the Black Panthers and took the Black Power ideology back to Nigeria
- started an autonomous zone in Lagos called Kalakuta Republic, where he decreed that everyone would follow what he claimed to be "traditional" African lifestyle, mainly consisting of having dozens of wives and smoking lots of weed
- almost all of his songs were over 15 minutes long, going over 30 minutes in his later career
- sang most of his songs in Nigerian Pidgin English, a lolcow language if there was one
- changed his name to Anikulapo, which means "He who carries death in his pouch"
- wrote a song called "Mattress" which is pretty much about how women only exist to please men
- married 27 of his dancers and backup singers after the Kalakuta Republic was raided and burned down by soldiers, only to later divorce them all
- fired his entire "Afrika 70" band and formed a new band called "Egypt 80" all because we wuz Egyptians
- after recording a song, he would never play it again, only playing new songs live which he'd frequently cut short and make his musicians start over. When combined with his typical song lengths it would often take an hour to get through a whole song live
- may or may not have died of AIDS depending on who you ask
I have to disagree: Fela was a badass who got the chicks and had one fucking kickass band; not a lolcow. A legend worth emulating. Maybe next life...
Honestly, it is hard to accuse a musician of lolcowdom because musicians actually have a skill or talent, which true lolcows lack. Some outsider musicians were kind of lolcows: certainly GG Allin was one, although when he was throwing punches and his own feces around, you didn't want to be in his way. Daniel Johnston was kind of one, but he was perhaps a little too talented and pathetic to be a complete one; he generated legitimate sympathy.
Utter humorless hacks who take themselves too seriously, like Chad Kroeger of Nickelback, almost qualifies, but he's too rich and bangs hot chicks.
Then there are guys like Anvil or Bobby Liebling of Pentagram, who had actual
movies made about their true life Spinal Tap-esque careers. But the Anvil guys are too likeable and Liebling is just a royal fuckup who at least is somewhat self-aware.
Roky Erickson of 13th Floor Elevators and Sky Saxon of the Seeds existed as weird sixties burnouts into the 21st century, but the schizophrenic Roky was at least modest and the cult refugee Sky was groovy if a bit grubby.
Colossal fuckups like Amy Winehouse come close to lolcows, but again, she lacked the humor element; she wasn't so entertaining as depressing.
Charles Manson was fairly amusing, but being a musician was more of a side job for him; I wouldn't count him as a committed musician.
Cher and Barbra Streisand are tempting, but too boring and rich.
Tiny Tim had an encyclopedic knowledge of pre-1920's music, which counts for something. He was more weird than lolcowy
Ronnie Radke of shitty Falling in Reverse seemed a likely candidate, but he seems to have mellowed out in recent years.
David Cassidy sure came close in his last years of life. So did Eddie Money if you get my drunk...er, I mean drift.
David Peel was a sweet guy.
Gary Glitter was on a roll for awhile until they finally locked him up for good.
The Shaggs? Nah...
Ashlee Simpson? Vanished too fast.
Liza Minnelli? Maybe if you find Judy Garland funny...
The thing about true lolcows is that they never have it together enough to make anything of themselves. The musicians I mentioned, which do include some abject losers, just weren't lulzy. Annoying, funny, weird, eccentric, fucked-up, yes. Famous people lack the street cred of real lolcows.