Shoemaker was married to Actress Nancy Allen in the early 1990s. He later married Actress Carolyn Ann Clark, and had two sons with her, Justin (b. 1998) and Jared (b. 2004), though they later divorced. He is currently married to Mika Shoemaker, with whom he has a son Jackson (b. 2009) and daughter Chloe (b. 2014).

Shoemaker has also had several television stand-up specials on networks such as Comedy Central and Showtime (titled "Daditude"). His signature character from his stand-up, the lecherous, deep-voiced "Lovemaster" eventually inspired a film in 1997.

In 2003, he founded LaughterHeals.org, a nonprofit group dedicated to using laughter as a healing modality. In 2014, Shoemaker published a book, Lovemaster'd: a Digital Journey to Love and Happiness, which details a long correspondence between himself and a women known only as "Leah" about their struggles with divorce and relationships.

In 2012 he received an honorary doctorate in Humanities/Humanistic Studies from California University of Pennsylvania.

His first acting role was a guest spot as an entertainment reporter on ABC’s Matlock. He later starred in a guest role on The Fresh Prince of Bel-Air, portraying the ghost of a boxer. He has since been a guest on many TV series, such as Sliders, Spin City, Diagnosis Murder, Parks & Recreation, and The Bold & The Beautiful. He has also acted in several feature films, such as Scream 2, Safe House, Pleasantville and National Lampoon's Totally Baked: A Potumentary. Most recently Craig has been writing for the hit Netflix series Fuller House.