Overweight, depressed improv actor James (Garlin) is a Second City cast member in Chicago. He lives with his mother and cheats on his diet. He quits his acting job on a sleazy television prank show, his girlfriend, Andrea, breaks up with him, and his agent, Herb, dumps him. When he visits his friend's daughter's elementary school for Career Day, he rambles about his problems, boring the kids, and embarrassing himself in front of the teacher, Stella (Hunt).
James relaxes in the evenings by lying on the hood of his car parked "in a great spot" beside Wrigley Field, and during the days by walking around the North Side of Chicago with his friend Luca, appreciating the buildings.
While wearing a pirate costume for a hot dog stand, James hears about a Chicago-based remake of Paddy Chayefsky's 1955 Marty, his favorite film, and one that mirrors his adult life. He knows the director but cannot get an audition. After walking out on his Compulsive Eaters Anonymous meeting, James goes to an ice cream parlor, where he meets "big-time hottie" Beth (Silverman), who recognizes him from Second City and offers him free ice cream. She asks him an obscurely lewd question, which she then cheerfully explains.
James, smitten, returns to the shop, where Beth takes him on adventures, including a shopping trip for her to try on underwear. They meet later after one of his comedy performances. One thing leads to another, and Beth volunteers to return to James's (and his mother's) apartment, where they have sex.
A day later, Beth succinctly dispatches James when he shows up at her apartment. Beth explains that she had just never been with a fat guy. Meanwhile, his role in Marty is given to a clueless young actor, real-life teen idol Aaron Carter.
As the story ends, James moves to his own apartment. He reconnects with Stella, the elementary school teacher, and continues acting.Jeff Garlin as James Aaron
Sarah Silverman as Beth
Bonnie Hunt as Stella Lewis
Amy Sedaris as Ms. Clark
David Pasquesi as Luca
Mina Kolb as Mrs. Aaron
Wallace Langham as Claude Clochet
Joey Slotnick as Larry
Richard Kind as Herb Hope
Rebecca Sage Allen as Andrea Hope
Roger Bart as Burl Canasta
Dan Castellaneta as Dick
Elle Fanning as Penelope
Tim Kazurinsky as Bill Bjango
Paul Mazursky as Charlie Perlman
Steve Dahl (cameo) as Father
Aaron Carter as himself as Marty
Gina Gershon as herself as Marty's mother
Alumni of the Second City
Production and distribution
"Garlin struggled to find financing, which twice fell through. He shot it in 18 days, but those days were spread out over two years," reported the Associated Press. IFC Films released the film on a non-traditional schedule, called "IFC First Take", part of IFC in Theaters. It appeared on pay-per-view cable television simultaneously with a limited theatrical release, in September 2007. The DVD followed about seven months later, April 15, 2008. In the meantime, IFC made a deal with Blockbuster, giving the video chain 60 days of exclusive rental and video on demand rights on each film. During interviews on Late Night with Conan O'Brien and Wait Wait… Don't Tell Me!, Garlin said that the title bothers Larry David because it ends in a preposition.
Rotten Tomatoes gave I Want Someone to Eat Cheese With a "fresh" rating of 74% with 34 positive reviews and 12 negative ones.
The New York Times called the "rambling" film "laid back and affectionate". In an appreciative review, Chicago-based Roger Ebert called it "a minor movie, but a big-time minor movie... If there is such a thing as a must-see three-star movie, here it is." However, John Maynard in The Washington Post scorned the movie, writing, "A better awkward title would be 'Random Events of a Failed Actor Plodding the Streets of Chicago.'"