He has also won acclaim for exploring the role Jews have played in the history of both comedy writing and the comic book industry.

In that series, he interviewed such comics luminaries as Al Jaffee, Stan Lee, Will Eisner, Art Spiegelman, Jerry Robinson, Paul Kupperberg, Trina Robbins, Drew Friedman, Judd Winick, Chris Claremont, Jon Bogdanove, and Joe Kubert.

In his role as an entertainment journalist, Kaplan has also interviewed recording artists, comedians, filmmakers, and cartoonists, including R. Kelly, 'N Sync, Carl Reiner, Susie Essman, Larry Gelbart, Sam Gross, Tom Leopold, Nora Ephron, and Lewis Black.

In 2010, he wrote "Disney Club Penguin: Shadow Guy & Gamma Gal: Heroes Unite" for Grosset & Dunlap.

Some of his best-known MAD pieces are the "Gulf Wars Episode 2: Clone of the Attacks"[3] poster, "What if Chris Rock Performed At A Bar Mitzvah?"

"[4] In Masters, Kaplan profiles the lives and careers of a diverse range of icons of the comic book genre, including Stan Lee (Spider-Man); Neil Gaiman (The Sandman); Marjane Satrapi (Persepolis, Art Spiegelman (Maus); Dwayne McDuffie (Static Shock); and Will Eisner (The Spirit).

[5] At an event at MoCCA celebrating the release of the book Kaplan was asked what the comic artists he interviewed—such as Eisner, Spiegelman, and Gaiman—have in common.