His stand-up routine is characterized by his eccentric appearance, falsetto voice, and surreal humor.

The unusual medieval-style bob haircut he sported early in his career, the exaggerated swings of his voice between registers, and his tendency to contort his body into awkward poses during delivery give him a bizarre stage presence. Some of his jokes play on the idea that he is crazy; for example:

"Some mornings it just doesn't seem worth it to gnaw through the leather straps." Some of his material is reminiscent of Steven Wright's one-liners or near one-liners with a surreal twist. For example:

"If you can make one person laugh, then you are already doing better than Tony Danza." "I was walking down the street, something caught my eye...and dragged it fifteen feet." "I don't have to tell you folks about scuba diving. So, that'll save some time." "Emo is really Swedish for, Honey, he bobbed to the surface again!" "When I was ten, my parents moved to Downers Grove, Illinois. When I was 12, I found them." Unlike Wright, however, Philips' persona is that of a strange, nerdy misfit, unlucky at love, looked down upon by society and prone to unconventional and occasionally antisocial behavior. Some more examples:

"I'm a great lover, I'll bet." "You know, a lot of girls go out with me just to further their careers...damn anthropologists." "I love to go down to the schoolyard and watch all the little children jump up and down and run around yelling and screaming...They don't know I'm only using blanks." "At my lemonade stand I used to give the first glass away free and charge five dollars for the second glass. The refill contained the antidote." "I ran three miles today... finally I said, 'lady, take your purse.'" "I was in a bar the other night, hopping from barstool to barstool, trying to get lucky...but there wasn't any gum under any of them." "Nothing gets me going in the morning like a nice, piping hot, cup of coffee. Oh, I've tried other enemas..." Philips has also had acting roles on television shows such as Miami Vice and The Weird Al Show (in The Weird Al Show, he looked directly into the camera, waved and yelled, "Hi Mom!....I'm sorry. Your cameraman looked just like my mother."). He's also voice-acted for the animated series Dr. Katz, Professional Therapist; Home Movies; and Space Ghost: Coast to Coast. He has appeared in films, including UHF (1989) and Desperation Boulevard (1998), and was associate producer of the film Meet the Parents (2000). He got the honorary title of associate producer because Meet the Parents was based on a short film that he did.

Philips has recorded three comedy albums. He has recorded a few songs, including "Treat Her Like a Lady." His album E=mo2 won the 1985 New Music Award for best comedy album. It has recently been re-released along with his Live at the Hasty Pudding Theatre album on a single CD.

On 8 August 1988, Philips married fellow surrealist comedienne Judy Tenuta (). They subsequently divorced. Tenuta has expressed embarrassment over having been romantically linked to Philips; Philips has dodged the issue in interviews. This denial has been frequent fodder for Howard Stern. Philips remarried in 2000.