- Was almost murdered twice in one week in Hartford, Connecticut by different people. As he admitted, "That's unusual." The first instance occurred when he was in a pub with Beth Henley. After a brawl with a man who was attacking Henley, he was held at gunpoint at the pub. Later that week, when he and Henley went to a pizza parlor next to the pub, where he was stabbed. Fortunately, the knife only partly penetrated his belt buckle.
- Has a form of ESP he calls "hearing tones". While working with David Byrne on his film "True Stories", he told Byrne about his gift, who was inspired to write the song "Radio Head" about him. The band Radiohead took its name from this song.
- Broke his neck in five places while horseback riding in Iceland underneath an active volcano after the wind picked he and the horse up off the ground and blew them off the road. He was required to wear a neck brace for three and a half months and maintains that the experience has taught him to cherish every day.
- To develop a plotline for the 1986 film True Stories (1986) he and rocker David Byrne once stared wordlessly for two hours at Byrne's wall. On the wall were hundreds of pencil drawings of ideas for the film by Byrne. That very night, he wrote a thirty-page treatment for the film and was soon hired as a writer.
- Once held hostage at gunpoint at a supermarket in Snyder Plaza in Dallas.
- One of the actor's heroes is his late aunt, 'Hermine Tobolowsky', known as the "mother of the Texas Equal Rights Amendment".
- Stephen was originally cast to play Tim Taylor's "Tool Time" co-host, named Glen, on Home Improvement (1991), but a scheduling conflict prevented him from appearing in the pilot. Richard Karn was cast as Al, a temporary replacement, and after taping a few more episodes, Stephen was still unavailable and thus Karn was kept on permanently.
- His name is pronounced tow-buh-law-skee. He is of Polish Jewish and Austrian Jewish descent.
- He has appeared in three films that have been selected for the National Film Registry by the Library of Congress as being "culturally, historically or aesthetically" significant: Thelma & Louise (1991), Groundhog Day (1993) and Memento (2000).
- Was the lead singer in the first band formed by guitar legend Stevie Ray Vaughan. They went to school together in Dallas.
Not true. Please change to: In 1970, Tobolowsky recorded two songs on an album of Dallas garage bands called "A New Hi." Stevie Ray Vaughan played lead guitar with them. It was Stevie's first studio recording. - Attended Southern Methodist University in Dallas, Texas, with actress Patricia Richardson and playwright Beth Henley during late 1960s and early 1970s.
- He played Principal Flutie in the unaired Buffy the Vampire Slayer (1997) pilot episode.
- Surfing channels in Vancouver recently, he watched himself getting older and balder in old episodes of Seinfeld (1989), the film Thelma & Louise (1991) and the made-for-TV movie The Marla Hanson Story (1991).
- Was nominated for a Tony award in 2002 as Best Featured Actor in a Play for his role in the revival of "Morning's At Seven".
- Inducted into the Texas Film Hall of Fame on March 7, 2013 in Austin, Texas.
- Played two characters with the last name "Ryerson". "Ned Ryerson" in Groundhog Day (1993) (movie) and "Sandy Ryerson" in Glee (2009) (TV).
- His aunt was the head librarian at Ben Franklin Junior High School in Dallas (now Hillcrest High School) for many years.
- Attended Kimball High School. High School Debate champ.
- Very good friends with cinematographer/director Robert Brinkmann.
- Edwin Tobolowsky is his third cousin.
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