#6. Courtney Love
I get what your angle is here, Courtney. With your self-inflicted wounds and bloody kitchen knife and neon nudity, you're trying to say that your world actually isn't very glamorous at all. The portrait is ironic, or in Courtney-speak, it's "iwronick."
Incidentally (and not that I knew the lyrics offhand or anything), this drawing is actually a perfect representation of the song "Celebrity Skin" by Hole:
When I wake up
in my makeup
it's too early
for that dress
wilted and faded
somewhere in Hollywood
I'm glad I came here with your pound of flesh.
Fine, I'm bragging. I knew every one of those lyrics offhand.
#5. Charles Manson
It's super weird that Charles Manson drew himself as a Pokemon. It's even weirder that his special ability is growing creepy beards. And it's the weirdest that he talked Charmander into killing Ash for him.
This portrait was sketched inside the walls of the California state prison, which is why it has that certain je ne sais quoi. Mansonchu go!
#4. Sylvester Stallone
Guess the name of this self-portrait a young Sylvester Stallone painted way back in 1977! Come on, guess! OK, I'll go first: Green Eye of the Tiger. Mona Lisa Sly.
Nope. The rendering of this chiseled, sallow, be-wife-beatered Stallone who has somehow managed to get himself stuck in the middle of a brick wall is called Trapped Ideals. Because, you know, art.
Incidentally, Sylvester Stallone's actual eyeballs are colored a lovely semi-aquatic-rodent brown and bear no resemblance to the emerald hue seen here. So: trapped ideals, indeed.
#3. Grace Slick
What's great about this portrait done by Grace Slick of Jefferson Airplane/Starship fame is that although she's naked and making devil horns, Grace has painted herself in a style one might find filling up the booths of a craft fair in rural Vermont. This technique just screams serving platters and decorative cookie jars. I mean, you could probably commission a tote bag* bearing this exact image from your mom's co-worker's Etsy shop -- and it would come with a free pair of macaroni earrings.
*Please, don't commission that tote bag.
#2. Joni Mitchell
It's surprising to find out that Joni Mitchell painted herself as Vincent Van Gogh (not to mention a little arrogant), but it's flat out alarming to learn that she cut off her ear and mailed it to Joan Baez. And let's not even get into that reproduction of Starry Night she created with her own feces.
Also, if "Turbulent Indigo" isn't Joni Mitchell's stripper name, then dammit, what is even the point of living?
#1. Wesley Willis
Wesley Willis' epic Magic Marker creation is exactly what a self-portrait should be! Funny, colorful, totally ready to high-five the shit out of you. Featuring his signature grid-marked buildings, this is just one of the hundreds of drawings Wesley produced during his 40 glorious years on this earth.
Let's all head-butt our computer screens in his honor.