by Gregg Bordowitz (1995) which appeared on public television, with Rakoff playing Vladimir Mayakovsky on whose poetry the film was based. His subsequent film appearances include performances as a librarian in Cheryl Dunyé's film The Watermelon Woman (1996), an appearance by the back of his head as Ben Baron, who is dismissive to Harper Lee, in Bennett Miller's Capote (2005), a non-speaking role as Boswell in Paul Dinello's Strangers with Candy (2005) (which was co-written by Amy Sedaris), and roles as a publishing boss in Bad Bosses Go to Hell (1997) and as a duplicitous director in Alison MacLean's film Intolerable. Rakoff can be seen in the Academy Award winning short film The New Tenants (2009). In the film he plays Frank, half of a gay couple who move into an apartment that was vacated unexpectedly. The film begins with Rakoff delivering a bitter, humorous but pessimistic monologue on life and death. Rakoff also adapted the screenplay for the film. Rakoff appeared as himself in the documentary Florent: Queen of the Meat Market (2009) about a local restaurant and in a film about the book State by State (2008), in which one of his essays is published. Television Rakoff appeared as modelling agent Rich Tuchman in As the World Turns, a television soap opera. He wrote about that experience in the essay "Lather, Rinse, Repeat", published in the collection Fraud. He also appeared as Todd in Cosby (1996–2000) and as Frank in the TV show Snake 'n' Bacon (2009). Stage Rakoff acted in the theater, including off-Broadway, notably in plays written by The Talent Family (David and Amy Sedaris). Those plays included the Obie award-winning One Woman Shoe 1995), in relation to which a critic writing in Newsday said that Rakoff "exuded quirky appeal", The New York Times said both that Rakoff was "hilarious" and that he delivered "a droll, impeccably sustained performance providing the necessary anchor". Rakoff also appeared in the Sedaris's The Little Freida Mysteries at La Mama (1997), of which The New York Times said Rakoff was part of a "deft ensemble", and which received a good review in Newsday. and in The Book of Liz (2001), in which he played various characters, including Nathaniel Brightbee, a member of a crypto-Amish order called "The Squeamish", who takes over Amy Sedaris's cheese ball operation. His performances were highly regarded by some critics. Rakoff portrayed Lance Loud on stage