Kaplow conceived the idea for
Me and Orson Welles while a student at
Rutgers University. He saw a photo in the periodical
Theatre Arts Monthly from 1937 with
Orson Welles with a young man. Kaplow wondered what the young man might have been thinking. He wrote the story, but it took about nine years to find a publisher.
Me and Orson Welles was a
New York Times bestseller and the film in 2008 starred
Zac Efron and
Claire Danes. The movie was filmed in the Gaiety Theatre on the Isle of Man. Kaplow's subsequent novel is a satire of writers, critics, and publishers. For
National Public Radio's
Morning Edition, Kaplow created "Moe Moskowitz and the Punsters," a series of musical and satirical pop-culture parodies. These musical parodies were released on two CDs:
Steven Spielberg, Give Me Some of Your Money and
Cancel My Subscription: The Worst of NPR. Kaplow was fired from NPR on three separate occasions, the first because of concerns that the Moe Moskowitz character was a Jewish stereotype, the second over the perceived quality of the segment's humor, and the third because
Cancel My Subscriptions CD release featured an unlicensed use of the NPR logo. Kaplow wrote the screenplay for Linklater's 2025 film
Blue Moon., for which he received an Academy Award nomination for Best Original Screenplay. ==Personal life==