Continued success beyond stand-up
In 1989, Wright and fellow producer Dean Parisot won an Academy Award for their 30-minute short film The Appointments of Dennis Jennings, directed by Parisot, written by Mike Armstrong and Wright, and starring Wright and Rowan Atkinson. Upon accepting the Oscar, Wright said, "We're really glad that we cut out the other sixty minutes." In 1992, Wright had a recurring role on the television sitcom Mad About You. He also supplied the voice of the radio DJ in writer-director Quentin Tarantino's film Reservoir Dogs that year. "Dean Parisot's wife Sally Menke is Quentin Tarantino's [film] editor, so when she was editing the movie and it was getting down toward the end where they didn't have the radio DJ yet, she thought of me and told Quentin and he liked the idea," Wright explained in 2009.
In 1995, Wright provided voiceover work for TBS's Disaster Area cartoon block.
Numerous lists of jokes attributed to Wright circulate on the Internet, sometimes of dubious origin. Wright has said, "Someone showed me a site, and half of it that said I wrote it, I didn't write. Recently, I saw one, and I didn't write any of it. What's disturbing is that with a few of these jokes, I wish I had thought of them. A giant amount of them, I'm embarrassed that people think I thought of them because some are really bad."
After his 1990 comedy special Wicker Chairs and Gravity, Wright continued to do stand-up performances, but these were largely absent from television, and he only occasionally made guest spots on late-night talk shows. In 1999, he wrote and directed the 30-minute short One Soldier, saying it's "about a soldier who was in the Civil War, right after the war, with all these existentialist thoughts and wondering if there is a God and all that stuff."
In May 2000, Wright and other Ding Ho alumni, including Lenny Clarke, Barry Crimmins, Steve Sweeney, Bill Sohonage and Jimmy Tingle, appeared at a reunion benefit for comic Bob Lazarus, who was diagnosed with leukemia.
In 2006, Wright produced his first stand-up special in 16 years, Steven Wright: When the Leaves Blow Away, originally aired on Comedy Central on October 21, 2006. On September 25, 2007, Wright released his second album, I Still Have a Pony, a CD release of the material from When The Leaves Blow Away. It was nominated for the Grammy Award for Best Comedy Album.
Beginning in 2008, Wright occasionally appeared on The Late Late Show with Craig Ferguson as a visiting celebrity, often dropping by to help with the fan-mail segment. He joined a small cadre of Hollywood comedy celebrities who supported the show.
