The group's songs, characterized by Katz's talk-singing, are typically short and lyrics-driven with a dry sense of humor and tend to share a thematic interest in anxiety and sociopolitical unease.

[1][2] After graduating from the University of California, Los Angeles, during the Great Recession, Katz began working in artists and repertoire for record labels.

[1][3] Tannen stated that she wanted to "be in a band that is not cool"; the group considered other names before Cheekface including Ryan Gosling's Huge Freakin' Delts and Plumping.

[3] Cheekface's first year was dedicated to songwriting; Tannen and Katz described the writing process as attempts to make one another laugh, with lyrics that successfully accomplished this ending up in the songs.

[3] However, in 2019 while playing a set at The Satellite in Los Angeles, Katz was startled when a small group of attendees sang along to every word in one of the band's tracks, temporarily causing him to forget several lines of his own lyrics.

[2] Zach Schonfeld in Alternative Press described their music as lyrics-driven with a dry sense of humor and characterized the group's songs as consisting heavily of one-liners, obscure name-drops, and references to bygone cultural moments.

[17] Cheekface described themselves as being influenced by "great American talk-singers" including Lou Reed, Stephen Malkmus, and Jonathan Richman, as well as by the alternative hip hop group Das Racist.

[1][3] In a 2022 review in Stereogum, Chris Deville compared Katz's singing style to that of Reed and Malkmus, as well as to James Murphy of the band LCD Soundsystem, Travis Morrison of The Dismemberment Plan, Jeff Rosenstock, The B-52's, and Devo.