DIGITAL ILLUSTRATION GALLERY

FIFTY WAYS TO LEAVE YOUR LOVER

Fifty Ways To Leave Your Lover, Valerie Caesar, 2025.

The other day, I woke up humming “Fifty Ways To Leave Your Lover,” and got to thinking about creating a movie-style poster that highlighted those folksy lyrics. Because the Paul Simon song came out in the ‘70s, I wanted to illustrate those rambling men using images of afroed and mutton-chopped brothers at the height of funky fashion, with bellbottoms sharp enough to cut a bitch. The imagined plot is like 5-8 different but intertwining tales about 5-8 different dudes scheming to leave their lovers in ways that are less than straightforward.

I went through quite a few versions that I’ll spare you of (except for the A Closer Look video below; that’s one of the old ones) before landing on this style, where I rendered photos of the men using a grainy brush, atop of and behind which we can see the title, accompanying lyrical directives, and monosyllabic names of these dudes. (It’s for both style and irony that I used the classic Martin I-AM-A-MAN font).

I don’t think Jack, Stan, Roy, Gus or Lee needed much encouragement to dip on his old lady, but the song really amuses me as a dude’s trifling-ass anthem of liberation. “You don’t need to discuss much!” LMAO. Typical. But I’d definitely go see this movie, just to make myself mad. Because these dudes are kinda fine!

A CLOSER LOOK

Watch this short video at the full screen setting to view an earlier and current versions of Fifty Ways To Leave Your Lover in closer detail.