As an actor, he was known for starring in the ABC sitcom Anything but Love from 1989 to 1992, and for playing the role of Prince John in the 1993 film Robin Hood: Men in Tights.

[4] His father, Bill (d. 1971), was co-owner of Ambassador Caterers in nearby Teaneck, New Jersey,[5] and his mother, Blanche, was an actress in community theatre.

[4] He graduated from Dwight Morrow High School in 1965 and attended Ohio State University where he attained a Bachelor of Science in Business Administration in Marketing four years later in 1969.

[13] By the mid-1970s, Lewis had appeared on The Tonight Show Starring Johnny Carson[14] and publications, such as the New York Daily News and New York magazine, were naming him one of the "new breed" or "class" of comedians; this list containing names such as Robert Klein, Lily Tomlin, Richard Pryor, George Carlin, Andy Kaufman, Richard Belzer, and Elayne Boosler.

[18] Lewis made his screen acting debut in Diary of a Young Comic, a 90-minute film that aired on NBC in 1979 in the timeslot normally reserved for episodes of Saturday Night Live.

[22] A satirical look at the Hollywood scene, Lewis stars in the film as Billy Gondola (born Gondolstein), a young Jewish comedian who leaves New York City to find fame in Los Angeles.

[22][23] The film features Bill Macy as Billy's father, Michael Lerner as his agent, and Stacy Keach as a landlord.

[23] Performers George Jessel, Dom DeLuise, Nina van Pallandt, and Gary Mule Deer make appearances in the film as themselves.

The latter film featured performances from Faye Dunaway, George Martin, Parker Posey, Howard Rollins, Spalding Gray, and Dianne Wiest, and was based on Gary Lennon's play Blackout.

[20][28] Into the 2000s, Lewis had recurring roles as a B movie producer on the sitcom Rude Awakening,[29] and as Rabbi Richard Glass on the family drama series 7th Heaven.

[33] Lewis also petitioned the editors of Bartlett's Familiar Quotations to include the idiom, which was also worked into the plot of Curb Your Enthusiasm during the episode "The Nanny from Hell".

[34] In response, Lewis told Entertainment Weekly that he traces popular usage of the line back to his early days on David Letterman's show.

[19] In a 1995 interview with the Santa Maria Times, Lewis discussed how John Candy's death the year prior had caused him to reflect upon his own life and career.

[7] In 2015, he released the book Reflections from Hell: Richard Lewis' Guide on How Not to Live; it contains his commentary and observations in the form of one-liners and other comedic premises, interspersed with images created by artist Carl Nicholas Titolo.