I don't recall when I became a fan of Drew Friedman's celebrity cartooning but it was not long after I first saw him in one of my favorite magazines — National Lampoon, I suspect. I was attracted for two reasons, one being the way he captured likenesses so well. And the other was that his choice of celebs to draw and the contexts into which he drew them suggested that that Friedman guy liked a lot of the same movie stars, Old Jewish Comedians, names-in-the-news and even other cartoonists that I liked. Also, I didn't have to get out the magnifying glass and search for NINAs in the hair and clothing of those he caricatured.
I later got to meet Drew and liked the artist, as well. So I really enjoyed a new documentary about him — Drew Friedman: The Vermeer of the Borscht Belt. It's not too long, the way a lot of those documentaries are and it's filled with famous folks talking about what an honor it was to be drawn by Drew. either in his early "stipple style" period or later when he developed a wider range of techniques. (Before I watched the video, I wondered if it would address his changeover and, yes, it does.) It's currently viewable, as is just about everything, on Amazon but also just about anywhere you'd expect to see this kind of thing. I recommend you seek it out.