Winick's Nuts and Bolts strip began running in the San Francisco Examiner in March of that year.
Winick, who is Jewish, was offended at David "Puck" Rainey's wearing of a T-shirt depicting four guns arranged in the shape of a swastika, and by Rainey's refusal to accede to Winick's request not to wear it.
After filming of the season ended, Winick and Ling moved to Los Angeles to continue their relationship.
By August 1994, Zamora's health began to decline. After being hospitalized, he asked Winick to substitute for him at a national AIDS education lecture. When Zamora died on November 11, 1994, Winick and Ling were at his bedside. Winick would continue Zamora's educational work for some time after that.
While working on Pedro and Me, Winick also began working on comic books, beginning with a one-page Frumpy the Clown cartoon in Oni Press’ anthology series, Oni Double Feature #4, in 1998, before going on to do longer stories, like the two-part Road Trip, which was published in issues #9 and 10 of the same book. Road Trip went on to become an Eisner Award nominee for Best Sequential Story.
Winick followed up with a three-issue miniseries, The Adventures of Barry Ween, Boy Genius, about a cynical, profane grade school whiz kid, who invents a myriad of futuristic devices that no one other than his best friend knows about. Barry Ween was published by Image Comics from March through May 1999, with two subsequent miniseries published by Oni Press, which also published trade paperback collections of all three miniseries. Barry Ween was also optioned by Platinum Studios to be adapted into an animated series, but to date, nothing has come of this.
Winick’s graphic novel, Pedro and Me: Friendship, Loss, and What I Learned, was published in September 2000. It was awarded six American Library Association awards, was nominated for an Eisner Award, won Winick his first GLAAD award, has been praised by creators such as Frank Miller, Neil Gaiman, and Armistead Maupin, and has been incorporated into school curricula across the country. Among its other awards are:
Winick’s work in mainstream superhero comics has received attention for storylines in which he explores gay or AIDS-oriented themes. In his first regular writing assignment on a monthly superhero book, DC Comics' Green Lantern, Winick wrote a storyline in which Terry Berg, an assistant of the title character, emerged as a gay character in Green Lantern #137 (June 2001) and in Green Lantern #154 (November 2001) the story entitled "Hate Crime" gained media recognition when Terry was brutally beaten in a homophobic attack. Winick was interviewed on Phil Donahue's show on MSNBC for that storyline on August 15, 2002, and received two more GLAAD awards for his Green Lantern work.
In 2003, Judd Winick left Green Lantern for another DC book, Green Arrow, beginning with issue #26 of that title (July 2003). He gained more media recognition for Green Arrow #43 (December 2004) in which he revealed that Green Arrow's 17-year-old ward, a former runaway-turned prostitute named Mia Dearden, was HIV-positive. In issue #45 (February 2005), Winick had Dearden take on the identity of Speedy, the second such Green Arrow sidekick to bear that name, making her the most prominent HIV-positive superhero to star in an ongoing comic book, a decision for which Winick was interviewed on CNN.
Winick’s other comic book work includes Batman, The Outsiders, and Marvel's Exiles. Winick was also responsible for bringing Jason Todd, the second character known as Batman’s sidekick Robin, back from the dead, and making him the new Red Hood, the second such Batman villain by that name. Winick also wrote a five-issue miniseries for DC’s Vertigo imprint called Blood & Water, about a young man with terminal illness whose two friends reveal to him that they are vampires, and that they wish to save his life by turning him into a vampire himself. Between September 2005 and March 2006, Winick wrote the four-issue Captain Marvel/Superman limited series, Superman/Shazam: First Thunder with art by Josh Middleton. Currently, Winick is continuing his work with the Marvel Family in a 12-issue limited series called The Trials Of Shazam! which is illustrated by Howard Porter. The series is intended to re-imagine the Shazam! mythos, the characters, and their roles in the DC Universe. He is currently the writer of Green Arrow and Black Canary and Titans. In November 2007, DC also released a Teen Titans East special (a prequel for Titans), which was also scripted by Winick.