He appeared in two 1968 episodes of The Monkees as well as having a cameo in the 1969 special 33 1/3 Revolutions per Monkee. He continued to work as a voice performer in the 1970s cartoon series Here Comes the Grump (as the title character) and in the second The Addams Family cartoon series (as Uncle Fester).

In addition to the Ed Sullivan Show, Taylor appeared on The Jackie Gleason Show in several guest appearances during the 1963-64 season as "the crying Comedian."

Taylor's first big live show was in 1966, when he went on a tour with Judy Garland and Eleanor Powell in Las Vegas. In 1981, Taylor appeared on Broadway when he replaced Mickey Rooney in the burlesque-themed musical comedy Sugar Babies. He was a frequent co-star with Debbie Reynolds in her live shows in Las Vegas, Reno, and Lake Tahoe. Taylor performed frequently in Atlantic City as well. In 2010, he appeared in the one-man show It Ain't All Confetti in North Hollywood, where he shared personal stories about his life and career.

Throughout the 1970s, Taylor was a frequent Celebrity guest panelist on TV game shows such as Hollywood Squares, To Tell the Truth, and The Gong Show, and substituted for Charles Nelson Reilly on The Match Game. He became a regular on Sid and Marty Krofft's Sigmund and the Sea Monsters, playing Sheldon, a sea-genie who lived in a conch shell. In addition, Taylor was also a regular on The Brady Bunch Hour, playing a role of neighbor/performer Jack Merrill. He also hosted a short-lived send-up of beauty pageants called The $1.98 Beauty Show, created by Gong Show producer/host Chuck Barris, in 1978. Taylor appeared as a Celebrity on the 1990 version of Match Game. In 1979, he was the voice of C.J. from the Hanna-Barbera TV movie Scooby Goes Hollywood. Other appearances include the television show The Kids in the Hall. He was referred to as Uncle Rip by Buddy Colem one of the show's characters. He also appeared as himself in the movie Wayne's World 2, one of the special guests invited to "WayneStock" after being visited in a dream by Jim Morrison.

Taylor has made occasional appearances in movies, usually in broad comedies like The Happy Hooker Goes to Washington (1977) and the R-rated Deep Throat parody Chatterbox (1977). In Cheech and Chong's Things Are Tough All Over (1982), he picks them up in the middle of nowhere driving a convertible full of props. Rip then proceeds to drive them to Las Vegas and telling jokes the whole way and moving Chong to tears from laughter (and, later, tears because he won`t stop). In Amazon Women on the Moon (1987) a funeral Service turns into a Celebrity roast when guest Rip Taylor shows up to "honor" the deceased. In 1993, Taylor appeared in Tom and Jerry: The Movie (1992) as Captain Kiddle and in Wayne's World 2. In 1993's Indecent Proposal as Demi Moore's boss, he appears without his toupee. He was also in the 1990 summer movie DuckTales the Movie: Treasure of the Lost Lamp as the voice of the Genie.

Taylor appeared uncredited on a December 1994 edition of WWF Monday Night Raw to assist in a push being given to Jeff Jarrett.

Taylor is an accomplice of the Jackass crew. In 1995, he performed the intro for the Bloodhound Gang's Use Your Fingers album, and in 2002, he appeared in the final scene of Jackass: The Movie, wielding a pistol that, when fired, released a sign that read "The End." (Taylor's section of the film was originally considerably longer, and ended with him complaining about the heat, and fanning himself with his toupée. This footage was included on the DVD of the film.) He did the same thing at the ending of Jackass Number Two and Jackass 3D. In the credits of the 2005 remake of The Dukes of Hazzard, Taylor shows up in the blooper reel.

In 1997, Taylor appeared in a segment on the show Beyond Belief: Fact or Fiction. He played the role of Elmo Middleton in the segment "The Man in the Model T". Also in 1997, he appeared as himself on the sitcom Brotherly Love in the episode "Easy Come Easy Go". He also portrayed Chief Undersecretary Wartle in the graphical adventure game Zork: Grand Inquisitor in 1997. In 2003, Taylor also appeared as himself on Will & Grace. In 2005, he appeared as himself on an episode of George Lopez. Taylor guest-starred as chef "Rappin' Rip" in four episodes of Life with Bonnie. He guest starred in The Suite Life of Zack & Cody episode "Loosely Ballroom" as Leo. He is also in some episodes of The Emperor's New School as the voice of the Royal Record Keeper. He was also in the Jetix animated series Super Robot Monkey Team Hyperforce Go!. He made a special guest appearance at the end of the 1,000th episode of G4's video game review show X-Play. He made a guest appearance on a 2012 episode of The Aquabats! Super Show!, where he played a genie reminiscent of his character on Sigmund and the Sea Monsters.

In 2006, Taylor appeared as the grand marshal of Washington, D.C.'s Capital Pride parade. Although he has been referred to as "openly gay", in a 2009 interview for "Ask the Flying Monkey", Brent Hartinger recalls receiving an email from Taylor stating: "You don’t know me to summarize that I am openly gay. I don’t know that you’re not an openly heroin user. You see how that works? Think before you write." Taylor was married to showgirl Rusty Rowe but later divorced.

Taylor was born in Washington, D.C., the son of Elizabeth, a waitress, and Charles Elmer Taylor Sr., a musician. As described in his 2010 one-man show It Ain't All Confetti, Taylor had a tough childhood, which included being molested while in foster care and having to deal with bullies in school. As a young man, Taylor worked as a congressional page before serving in the Korean War while in the U.S. Army Signal Corps.