As the founder of influential proto-punk band The Modern Lovers, Richman had striven to convey authentic emotions and storytelling with his music.

I, Jonathan continued this aesthetic with simple and sparse rock and roll arrangements, and straightforward lyrics about everyday topics, such as music, parties, summer, and dancing.

Songs on the album addressed topics such as backyard parties ("Parties in the U.S.A"), memories of neighborhoods in which Richman had lived ("Rooming House on Venice Beach" and "Twilight in Boston") and his admiration of his primary musical inspiration, the Velvet Underground ("Velvet Underground").

[4] Also notable is a revisited and somewhat longer version of "That Summer Feeling," which was first recorded on 1983's Jonathan Sings!

The album helped increase Richman's cultural profile, which would include a 1993 appearance on Late Night with Conan O'Brien during which Richman performed one of the album's songs, "I Was Dancing in the Lesbian Bar.