Glassman moved to Los Angeles in 2008 where he continued to perform stand-up comedy.[4] His career gained traction after performing regularly at The Comedy Store.[4] In 2013, he was invited to the New Faces showcase at Just for Laughs comedy festival.[4] He appeared in an episode of Adam Devine's House Party in the show's second season.[8]
Writer-producer Bill Lawrence invited Glassman and fellow comedian Brent Morin to audition for his sitcom Undateable after watching both comedians perform at the Hollywood Improv.[4] Glassman and Morin each won roles in the show, which also stars Chris D'Elia, Ron Funches and David Fynn.[4] Glassman played the part of Burski, a regular patron of the bar owned by Morin's character.[4] While working on the show, Glassman pitched an idea to Lawrence that became the NBC-produced web series spin-off The Sixth Lead.[9] Written, directed by, and starring Glassman, The Sixth Lead follows him during his day-to-day experiences as "the sixth lead" in Undateable's cast.[9][10] Similar in style to the series Curb Your Enthusiasm, the series provides the viewer with a semi-fictionalized, behind-the-scenes look at Undateable's production and includes appearances by Lawrence and other cast members, as well as appearances by Zach Braff as himself.[9][11] Glassman edited the series into a short film that won Best Short Film at the 2016 IFS Festival, held by the Independent Filmmakers Showcase in Los Angeles.[11][12]
In 2019 he launched his podcast, Take Your Shoes Off.[5] The show mainly features interviews with comedians and others in the entertainment industry, sometimes featuring scenes briefly superimposed with digital animation or dramatized scenes between himself and his guests for comedic effect.[5][13] His show also features advertisements directed by Glassman for Marshall Carpet One and Rug Gallery, the carpet store co-owned by his father.[5]
In 2022, Glassman starred in the comedy drama series As We See It. Based on the Israeli series On the Spectrum, the show revolves around the lives of three roommates who are autistic.[14] The roommates are played by actors on the autism spectrum, including Glassman, who was diagnosed with autism in adulthood.[5][14] He also starred as Edward in the ABC sitcom Not Dead Yet, which premiered in February 2023.[2][15] Glassman's character was autistic and the roommate of the character played by the show's lead Gina Rodriguez.[15] The show ran for two seasons before being canceled in 2024.[16]
Rick was in six McDonald's commercials, five of which were voice overs and one was a live action appearance.[17]
Personal life
Glassman was diagnosed with level 1 autism (formerly known as Asperger syndrome) in the late 2010s.[5] He told Forbes that, since his diagnosis, "All of these seemingly unrelated obstacles became patterns that made sense... It's something that I was and am proud of."[14]