From November 1990 until September 1995, he co-hosted, with NPR producer Gary Covino a weekly, local program on Chicago Public Radio called The Wild Room. In 1993, Glass said, “I like to think of it as the only show on public radio other than ‘Car Talk’ that both [NPR news analyst] Daniel Schorr and [lead singer/guitarist of Nirvana] Kurt Cobain could listen to. I think it’s appropriate that the show [which aired on Friday evenings] is on a station that most people don’t listen to at a time when most people won’t hear it. And the fact that public radio never puts a new show on the air or takes any off is definitely to our advantage.” During this time, he spent two years reporting on the Chicago Public School System -- one year at a high school, and another at an elementary school. The largest finding of his investigations were that smaller class sizes would contribute to more success in impoverished, inner-city schools.
In 1995, the MacArthur Foundation approached Torey Malatia, general manager of Chicago Public Radio, with an offer of $150,000 to produce a show featuring local Chicago writers and performance artists. Malatia approached Glass who countered that he wanted to do a weekly program with a budget of $300,000. In 1998, Covino told the Chicago Reader, "The show he proposed was The Wild Room. He just didn't call it The Wild Room. Covino continued to produce the Wild Room until February of 1996.
Glass invited David Sedaris to read his essays on NPR, which led to Sedaris's success as an independent author; Glass also produced Sedaris' commentaries on NPR.
Since 1995, he has hosted and produced This American Life, from WBEZ. The show was nationally syndicated in June 1996 by Public Radio International and has been national ever since. PRI was eager to take on the program even as NPR passed on the program.
It reaches over 1.7 million listeners on over 500 stations weekly, with an average listening time of 48 minutes. Glass can be heard in all but one episode.
On November 17, 2005, This American Life celebrated its 10th anniversary. The following week, as a special show celebrating the anniversary, the first episode, "New Beginnings", was re-broadcast. Prior to this, the first episode had never been aired outside of Chicago. When the first episode was broadcast in 1995, the show was known as Your Radio Playhouse. That first episode includes interviews with talk-show host Joe Franklin and Ira's mother, as well as stories by Kevin Kelly, founding editor of Wired, and filmmaker, performance artist Lawrence Steger.
In May 2008, the This American Life radio show was broadcast live to over 300 movie theaters.
Interestingly, Glass' father was a radio announcer also during his youth, but Glass was not made aware of this fact until after he had begun his own radio career.
In October 2007, he published the anthology The New Kings of Nonfiction.
He also served as one of the executive producers of the 2006 feature film Unaccompanied Minors. It is based on the true story of what happened to This American Life contributing editor Susan Burton and her sister Betsy at an airport on the day after Christmas. Burton had already produced a segment on This American Life about the same experience before the story was adapted to film.
On March 22 2007, Glass and company began airing a television version of This American Life as half-hour episodes on the Showtime network. During an interview with Patt Morrison on 89.3 KPCC, Southern California Public Radio, Glass revealed that he lost thirty pounds for this venture.
Due to an encounter with objectors to a segment of his show, Glass became a vegetarian. He discusses this in an April 2007 appearance on David Letterman.
For a time, he dated cartoonist Lynda Barry and moved to Chicago in 1989 to be with her. He called Barry his "little ghetto girl" and she does not remember the relationship fondly. Barry is quoted in a 1998 Chicago Reader article as saying of Glass, "I went out with him. It was the worst thing I ever did. When we broke up he gave me a watch and said I was boring and shallow, and I wasn't enough in the moment for him, and it was over." In the same article, Glass is quoted on his feelings about their breakup: "I was an idiot. I was in the wrong. About the breakup... About so many things with her. Anything bad she says about me I can confirm. Barry has written a comic story about the relationship, entitled "Head Lice and My Worst Boyfriend," in her book One! Hundred! Demons!.
In August 2005, Glass married Chicago editor Anaheed Alani. Glass and Alani moved from Chicago to New York in March 2006.
On April 25, 2008, Glass appeared on The Late Show with David Letterman, where he discussed his level of testosterone, his affinity for the Howard Stern radio program, and his recent adoption of a pit bull. One of the anecdotes was about the calm demeanor of his newly rescued dog and how people are afraid of it, but walking down the street it will cower away from even the smallest of dogs. He also mused that he was glad his dog did not realize that a visiting dog, who comes over with hired trainers for socialization purposes, is not actually there to just be friends. Glass has to pay for this dog to come over and play, which, if his dog could comprehend the situation, would probably break her heart.
Noted composer Philip Glass is his father's first cousin.