My mom's boss asked her to ask me to draw caricatures of his parents, and him and his wife. It's been almost two solid years since that was actually how I made my living (and honestly, I hated doing it for the most part-- which is due entirely to the work environment itself), so I was skeptical. But I think they turned out okay, and they all loved them. I think I've gotten myself suckered into more work as a caricature artist though!
Excuse the glare-- I didn't think to take pictures myself and had him do it after he'd already received them and had them framed.