The 12 Most Ridiculous Celebrity Self-Portraits

The art of rendering one's own image on canvas is still going strong -- even in this era of the much more elegant iPhone mirror pic. As with everything else, celebrities do self-portraits better than us laypeople. Or at least they do them much, much weirder.
The 12 Most Ridiculous Celebrity Self-Portraits

Because human beings like nothing more than their own stupid faces, self-portraiture has been an enduring form of artistic expression since basically the beginning of time (the Biblical Adam could, in fact, be considered the first self-portrait).

Popularized by the Renaissance masters, the art of rendering one's own image on canvas is still going strong -- even in this era of the much more elegant iPhone mirror pic. As with everything else, celebrities do self-portraits better than us laypeople. Or at least they do them much, much weirder.

#12. Pierce Brosnan

Pierce Brosnan

Something between Bruce Willis in Die Hard 3 and McBain from The Simpsons is what Pierce Brosnan sees whenever he looks in the mirror.

I bet you looked at this portrait of Pierce and immediately picked out its best part. And I bet you think it's the blue car in the background exploding into a Michael Bay of flames (that's the collective noun for that, FYI). Or maybe you're partial to that sad-face-emoticon mustache, or those badass shades that came free with the family-sized bag of sunflower seeds at 7-Eleven. Perhaps your favorite part is even Mr. Brosnan's magenta pixie cut -- "Hairline be damned," says Pierce. "I will let my inner Kelly Osbourne run free!"

But you're wrong. The best part of this painting is its intricately rendered chest hair, a detail that lets us know that although Pierce took liberties with skin color, hair color and realism in general, he isn't cutting any corners where his masculinity is concerned. No sir: Those loopy black hairs promise us that had Pierce decided on a full-body portrait, he would have made his penis a python.

#11. Marilyn Manson

Marilyn Manson

Well, now we know what Marilyn Manson looks like in his birthday suit. Before the lipstick comes out and the monster-eye contacts go in and the bucket of baby powder gets dumped from the ceiling, Carrie-style, Marilyn Manson is nothing but a skinny, almost innocent-looking homunculus.

A skinny, innocent-looking homunculus who happens to have surprising insight into the psychology of school shootings.

#10. David Bowie

In addition to showcasing impressive technical skill, this painting also proves that David Bowie has a pretty decent sense of humor. No ordinary idealized self-portrait, the image above is a reference to an incident that occurred at a Norwegian concert in 2004, when someone in the crowd threw a lollipop at the singer. The sucker hit Bowie smack-dab in the eye, lodging itself in between his eyeball and his socket.

Escaping relatively uninjured, Bowie painted his interpretation of the incident a few years later -- and inexplicably gave himself the hands of a 6'10" NBA power forward.

#9. Matthew Gray Gubler

Matthew Gray Gubler

Criminal Minds actor Matthew Gray Gubler is exceedingly handsome.


The man portrayed in this portrait looks like he contracted walking pneumonia five days into a bath salts bender, tripped over a zombie, landed face-first into his grandmother's makeup bag, and had an allergic reaction to everything inside of it.

#8. Rosie O'Donnell

CBS News

I have to wonder if Rosie O'Donnell is using papier-mache as a metaphor here. Something about the many masks an American celebrity must wear just to get through the day unscathed. Which layer of Rosie is the real layer of Rosie?

Anyway, shut up, Rosie O'Donnell.

#7. Ronnie Wood

Ronnie Wood

Inside Ronnie Wood is a smaller Ronnie Wood, and inside that Ronnie Wood is an even smaller Ronnie Wood. The smallest Ronnie Wood has a tattoo of the first Ronnie Wood, and all the Ronnies live in an airbrushed Astro van that plays the obscene version of "Start Me Up" on a loop.

The Rolling Stones' guitar player is responsible for a ton of portraits of famous rock 'n' rollers (Mick Jagger, Bob Dylan, Jimi Hendrix), but none are quite as poetic as this one he painted of himself. When he set brush to canvas on his self-portrait, it's like he was begging to one day see this design on an overpriced T-shirt you can buy on a boardwalk somewhere. (It's a very special kind of immortality.)

#6. Courtney Love

The Sun

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

Charlie 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

NY Post

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

Asylum Records

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

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.

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