Bob Dassie

Nationalities

Chicago New York City Los Angeles Edinburgh United Kingdom United States

Bob Dassie is a Chicago-born improviser, performer, and teacher who trained at iO Chicago beginning in the early 1990s and has remained active across iO Chicago, iO West, UCB New York, and UCB Los Angeles. He performed on multiple iO ensembles including The Armando Diaz Experience and Baby Wants Candy, and formed Dasariski, a critically recognized long-form trio, with Rich Talarico and Craig Cackowski, whom he met at iO in 1992. With his wife, comedian and MADtv alumna Stephnie Weir, he created WeirDass, a two-person show developed at iO West in Los Angeles. His television credits include Community (NBC), Review (Comedy Central), The Comedians (FX), and The Spoils of Babylon (IFC). He has taught at iO Chicago, iO West, UCB, and the WGImprov School, and has led workshops across North America, the United Kingdom, and Singapore.

Career

Bob Dassie grew up in Greenwood, Illinois, a suburb outside Chicago. He watched Second City shows as a child and eventually enrolled in classes there, and later began training at iO Chicago (then Improv Olympic) in the early-to-mid 1990s.

At iO Chicago, Dassie met Rich Talarico and Craig Cackowski in 1992, collaborators with whom he would work across multiple ensembles over the following decades. Together, the three performed in ensembles including Mr. Blonde, Close Quarters, Baby Wants Candy, Trio, Cog, Quartet, and The Armando Show. He also performed with The Armando Diaz Experience, iO's ensemble performing the form Armando Diaz developed.

Baby Wants Candy, in which Dassie performed, is a fully improvised musical ensemble that performs complete improvised musicals using a live band. The ensemble performed at the Edinburgh Festival Fringe, where Dassie's castmate included Jack McBrayer, who later became known for his role as Kenneth on NBC's 30 Rock.

In the late 1990s, Dassie and actress Stephnie Weir, who was cast on Fox's MADtv (where she remained from 2000 to 2006), began a personal and professional relationship that developed into the two-person show WeirDass. The couple met during a five-week Edinburgh Festival Fringe run with an iO Chicago ensemble. After Weir was cast on MADtv, they relocated to Los Angeles, where WeirDass developed as a format at iO West. The show toured nationally, including performances in Portland at Curious Comedy.

In Los Angeles, Dassie also performed with Dasariski, a long-form trio with Rich Talarico and Craig Cackowski whose name is a portmanteau of their three surnames. The ensemble performed at iO West, where they played to sold-out houses, and at the Hollywood Fringe Festival. Dasariski's approach was described as slow play long-form, a single audience suggestion expanded into a half-hour to hour-long improvised piece emphasizing believable characters and relationships over game-based pattern work.

Dassie has taught at iO Chicago, iO West, UCB New York, UCB Los Angeles, and the WGImprov School, as well as leading workshops across North America, the United Kingdom, and Singapore. His approach to teaching emphasizes work ethic and positive scene choices.

His television credits include Community (NBC), Funny or Die Presents (HBO, in Carpet Bros. alongside Tim Meadows, David Spade, and Will Ferrell), Review (Comedy Central), The Comedians (FX), The Spoils of Babylon (IFC), and Monk. His film credits include Casa de mi Padre.

Historical Context

Dassie's career traces the institutional path that connected iO Chicago to both Second City and the west coast improv ecosystem during the 1990s and 2000s. His meeting with Rich Talarico and Craig Cackowski at iO Chicago in 1992 produced a collaboration that persisted across five institutions over two decades, reflecting the degree to which ensemble loyalty at iO tended to follow performers through institutional transitions rather than dissolving at the city or program level.

Baby Wants Candy's performances at the Edinburgh Festival Fringe during this period placed iO Chicago's improvised musical form within the international comedy festival circuit, and the ensemble's roster at Edinburgh included performers, such as Jack McBrayer, who subsequently developed significant television careers.

The development of WeirDass at iO West after Stephnie Weir's relocation to Los Angeles for MADtv illustrates a common dynamic in the Chicago-to-Los Angeles pipeline of the early 2000s: the institutional structures of iO West and UCB Los Angeles functioned as performance homes for Chicago-trained performers who relocated for television work but continued to perform long-form improv as a primary artistic practice.

Dasariski's description as a slow play ensemble and its sold-out runs at iO West reflect the reception in Los Angeles of a long-form approach distinct from the Harold and the UCB game-based forms that dominated that market. The ensemble's continued production at the Hollywood Fringe Festival extended its reach beyond institutional theater venues.

Teaching Philosophy

Dassie has taught at iO Chicago, iO West, UCB New York, UCB Los Angeles, and the WGImprov School, and has led workshops internationally in the United Kingdom and Singapore. His teaching approach emphasizes work ethic within ensemble contexts and making positive, committed choices in scenes rather than defaulting to deflection or negation. His experience across multiple long-form formats, including Harold-based work at iO, the Armando form, improvised musicals with Baby Wants Candy, and the slow play approach of Dasariski, has given him a curriculum grounded in format diversity rather than single-system instruction.

Legacy

Dassie's involvement across iO Chicago, iO West, UCB, and Baby Wants Candy situates him in the connective tissue between the Chicago long-form tradition and its Los Angeles transplantation during the 1990s and 2000s. His ensemble Dasariski, formed with Rich Talarico and Craig Cackowski, produced a working model of slow play long-form that operated outside the Harold and game-based UCB formats and achieved sustained recognition at iO West and the Hollywood Fringe Festival.

Baby Wants Candy's Edinburgh performances, in which Dassie participated alongside Jack McBrayer and others, placed iO Chicago's improvised musical format in front of international festival audiences during a period when the form was establishing itself as a viable long-term theatrical product. The ensemble's subsequent sustained run established the fully improvised musical as a commercially presentable format.

His teaching across North America, the United Kingdom, and Singapore extends his influence beyond the Chicago-Los Angeles improv corridor into international training contexts, reflecting the broader dissemination of iO and Harold-based pedagogy through individual practitioners rather than institutional expansion.

Early Life and Training

Bob Dassie grew up in Greenwood, Illinois, a suburb outside Chicago. He watched Second City performances as a child before enrolling in classes there and subsequently training at iO Chicago in the early-to-mid 1990s.

Personal Life

Bob Dassie is married to Stephnie Weir, a comedian and actress known for her seven seasons as a cast member on Fox's MADtv (2000-2006). The two met during a five-week Edinburgh Festival Fringe run with an iO Chicago ensemble in the late 1990s and subsequently collaborated on WeirDass, a two-person show developed at iO West in Los Angeles.