I remember watching a lot of The Real World: San Francisco in 1994, when Judd was part of the cast of the third season. Around that time, he was working on Nuts and Bolts, a daily comic strip. He dated a lot, but had a crush on med student Pam that wasn't really addressed on the show. He was also roommates with Pedro Zamora, who was HIV-positive. I recommend picking up Pedro & Me, the graphic novel published in 2000. In case you don't follow RW (and I can't say that I blame you, especially after the last decade), Pedro died in November 1994, the day after the final episode of the season aired. Judd and Pam wound up becoming a couple.
Judd would go on to create Frumpy the Clown before being recruited by Oni Press to writing and drawing "Road Trip" for Oni Double Feature. Next, he created The Adventures of Barry Ween for Image Comics, which was centered on a foul-mouthed boy genius. It was hysterical. He would do two more miniseries featuring Barry for Oni. Soon, he was picked up by DC Comics to succeed Ron Marz on writing chores for Green Lantern, and he would go on to write such titles as Exiles, Green Arrow and Outsiders. Around 1999-2000, I interviewed Judd twice. I had a tentative agreement with a magazine for an article. He was very nice about it. As I got more into reality television, I liked Judd as an example of somebody who came off as a putz winding up with a public career on his terms. Also, he was part of a panel that previewed The Real World: New Orleans and Road Rules: Maximum Velocity Tour, probably to increase his visibility for Pedro & Me. I reckon the highlight was him saying that Melissa and her parents deserved their own show.
I've met Judd in-person all three times at Comic-Con International in San Diego. I got sketches from him of Barry Ween and Jeremy Ramirez (Barry's hyperactive best friend). In 2009, I received a quick sketch of Juniper Lee, who had a show on Cartoon Network for a few seasons.
The sketch I remember most from Judd came at Wizard World Philadelphia in 2002. It was the first year of that convention, and I went as far as staying over in the city. This was back before I became comfortable with making long-distance commutes. Two days before the con started, Green Lantern #150 came out. Written by Judd, it marked a major turning point for Kyle Rayner, and it included a costume overhaul from Jim Lee. I wound up getting a sketch of Kyle from Judd. And years later, I got a t-shirt with Kyle's new emblem on the chest. I only wear it when I'm at cons.