For some reason, Will Smith has always been difficult for me to draw.  He should be easy, with those ears, unique eyes, wide nose… but he’s not.  Caricatures are a mystery sometimes.

When we teach caricatures to new artists, we spend the most time on realistic proportions.  Every caricature artist should be able to draw someone accurately before they commit to exaggeration.  In my case, it’s a fallback.  This is an old drawing of Will Smith, but I still remember trying several times to capture the likeness, then just falling back to a more realistic sketch and exaggerating the ears.  So it’s still a caricature… but I’ve seen much more interesting versions from other artists online.  What I like best about this one it the negative shape of his shirt.

It’s the original Captain Kirk and Mr. Spock, William Shatner and Leonard Nimoy.  This caricature is from 2008 I think.  I found this great photo of a really young Shatner and a really young Nimoy:

I love the super old phaser in this photo.  Also, I just found out that “Phaser,” isn’t a word in Google’s dictionary.  Surprising!  Guess they don’t have that many nerds on staff.

The light in the photo wasn’t that exciting, so I made up my own.

I’ve said it before:  Drawing a caricature of Johnny Depp as Captain Jack Sparrow is almost like cheating.  He’s a character so covered in makeup and wigs and ornaments and hair that, even if you get the features in kind of the wrong places and exaggerate the wrong things, it still is going to look like Captain Jack Sparrow.  In fact, every time I see a Captain Jack impersonator posing for photos on the Strip, I think, “That’s a pretty good Captain Jack Impersonator.”  This caricature is from ’07.  Looking back, I don’t love the likeness of Johnny Depp.  But even so, it’s still unmistakably Jack Sparrow.

Orlando Bloom is another story.  Always had a hard time making fun of that guy’s face.  It shouldn’t be too difficult… wide face, small lips, sharp cheeks and jaw.  But apparently I’m not alone… an image search for “Orlando Bloom Caricature” turns up several efforts, not of which can be said to nail the likeness.  Hey, some people are just hard to draw.

Keira Knightley is also a challenge.  This is a pretty old caricature, but I don’t hate some of the things I tried with her.  I might try wider instead of taller next time, but I like her nose, chin, and underbite.

Found this caricature from 2007!  Paris Hilton was at the height of her popularity.  I wanted to capture how skinny and elegant she was.  I still like this drawing, but I’m not sure about the chest on this one.  I kind of want to redo it in an more Hirschfeld-esque style.

In 2006, the Jonas Brothers were getting really popular, and I was experimenting with caricatures.  Looking at this now, I wish I hadn’t used any Artstix and instead finished the whole drawing with an ink brush.  This image would be better in black and white, with no tones in between.

But, you can tell who it is, and when it comes to caricatures, anything different is good.  I’ve been at this for a long time.

We used to keep bunches of celebrity magazines at the stand.  There would be piles of them.  And here in ’06, Tom Cruise and Katie Holmes were in every.  Single.  One.  Always.

Sometimes you draw people just because they’re in front of you all the time.  So that explains this caricature.  I was also happy to draw a meek Katie Holmes in the background with toothy Tom Cruise in the foreground.