In Smith's 1994 debut movie, Clerks, Flanagan was credited with four different roles (which made Kevin Smith, on the Clerks commentary, refer to Flanagan as "The Lon Chaney, Sr. of the 1990s"). Among these were the egg-obsessed guidance counselor, the cigarette protester who bought the cigarettes immediately after the protest, the customer offended by the lewd "jizz mopper" discussion, and the customer to whom Randal said the resident cat's name was "Annoying Customer." He also designed the clown animation that made up the View Askew logo, and appeared in the Soul Asylum video for "Can't Even Tell", directed by Kevin Smith.