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[[Tony Shalhoub]] originally auditioned for Guy Fleegman until [[Sam Rockwell]] won the role. Shalhoub was then cast as Fred Kwan<ref name="io9"/> and worked with Parisot to develop the character. Kwan was loosely based on [[David Carradine]], who was a non-Asian in an Asian role in the television series ''[[Kung Fu (1972 TV series)|Kung Fu]]''. Additionally, it was rumored that Carradine frequently acted while [[Substance intoxication|under the influence of drugs]]. Although Shalhoub could not overtly portray a "stoner" in a PG-13 film, he insisted that Kwan should always be shown eating to subtly reference the stoner stereotype.<ref name=MTV />
Rockwell, who wanted to develop a more serious dramatic acting career, initially considered declining the role after he was cast. He eventually recognized that several successful dramatic actors had done comedy roles early on, and Rockwell's friend [[Kevin Spacey]] persuaded him to take the part.<ref name=MTV /><ref name="thr dec2019"/> He was the last of the main actors to be cast.<ref name="thr dec2019"/> Rockwell fashioned Fleegman after cowardly characters from other films, such as [[John Turturro]]'s Bernie in ''[[Miller's Crossing]]'', [[Bill Paxton]]'s Private Hudson in ''[[Aliens (film)|Aliens]]'', and [[Michael Keaton]]'s "Blaze" in ''[[Night Shift (1982 film)|Night Shift]]''. Rockwell drank a lot of coffee before certain scenes to help create the over-excitement and jitters associated with the character.<ref name=MTV /> Rockwell's character's name, Guy Fleegman, is
[[Daryl Mitchell (actor)|Daryl Mitchell]] had worked with Parisot on ''Home Fries'', and Parisot felt he was the perfect choice to play Webber.<ref name="thr dec2019"/> [[David Alan Grier]] was the second choice for Webber.<ref name=MTV />
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