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Holmes has appeared on Comedy Central's Premium Blend, as a regular panelist on VH1's Best Week Ever, and on VH1's All Access.[3] His cartoonshave appeared in The New Yorker.[4] In 2010, he performed on John Oliver's New York Stand Up Show as well as Late Night with Jimmy Fallon. On February 26, 2010, he performed his first television special on the series Comedy Central Presents. On March 21, 2011 and on November 17, 2011, he appeared on the TBS talk show Conan.

Holmes has provided the voices for several of the characters on Comedy Central's cartoon Ugly Americans. He was the voice of the E-Trade baby on several television commercials and was also credited as a writer for those commercials.

He wrote for the NBC primetime sitcom Outsourced and also wrote for the Fox sitcom I Hate My Teenage Daughter prior to its cancellation in May 2012.

Holmes released his first album, Impregnated With Wonder, on iTunes on November 15, 2011. It was named one of the best comedy CDs of 2011 byThe A.V. Club.[5] In 2013, he released his second album, Nice Try, The Devil, which was also named as one of the best comedy CDs of 2013 by the Onion A.V. Club.

Holmes is also known for his comedic portrayal of Batman in CollegeHumor's internet series Badman. The series recreates scenes from Christopher Nolan's Batman films with a comedic twist, such as Batman appearing completely incompetent or sex-obsessed.

Damon started doing stand-up comedy in 1982. His earliest film appearance was a brief cameo as an effeminate hotel employee in the 1984 Eddie Murphy film Beverly Hills Cop. He was briefly on Saturday Night Live as a featured performer, before getting fired for playing his character as a flamboyant gay cop instead of a straight cop. He went against the script during the live performance. In the Saturday Night Live bookLive From New York, it was stated that Wayans did this largely due to growing frustrations that his sketches were not being considered for the show and increasing stress. He also appeared in the syndicated TV series Solid Gold during the 1980s as astand-up comedian. After that, he went on to co-create and appear in the TV-show In Living Color from 1990 to 1992, part of a team that was nominated for Emmy Awardsall three years.

After In Living Color, he starred in films such as The Last Boy Scout, Major Payne andThe Great White Hype and wrote and starred in the film Blankman. He also appeared in Janet Jackson's video "The Best Things in Life Are Free" and was considered for the role of The Riddler in Batman Forever (the role went to Jim Carrey, his co-star from In Living Color and Earth Girls Are Easy).

In 1996, he produced Waynehead, a cartoon for the WB, loosely based on his own childhood growing up in a large family, starring a poor boy with a club foot. The show only lasted a season due to poor ratings. From 1997 to 1998, he was the executive producer of 413 Hope St., a short-lived drama on the FOX network starring Richard Roundtree and Jesse L. Martin.

In 1998, he starred in a short-lived comedy titled Damon, in which he played a Chicago detective. It aired on FOX. In 1999, his New York Times bestselling book Bootleg with co-author David Asbery was published; it is a humorous compilation of his observations about family.[6]

For his role in the ABC comedy series My Wife and Kids from 2001 to 2005, Wayans received four International Press Academy "Golden Satellite Award" nominations, in addition to four Emmy awards nominations for his acting and directing in the 1990s series In Living Color.

In 2006, he began starring in The Underground, a sketch comedy series on Showtime. His son, Damon, Jr. also stars on the show. He hosted the 2006 BET Awards which was held at the Shrine Auditorium in Los Angeles, California on June 27, 2006.

In 2011, he also added author of a serious fictional novel to his credits with "Red Hats" which is the story of a suicidal 65-year-old woman who finds friendship and happiness when she joins the Red Hat Society.

As of 2014, Wayans continues to perform stand up comedy and has developed apps including Flick Dat (A new way to send and receive business cards, photos, videos) and Diddeo (an easy way to make your own music videos).[7]

Super Secret Comedy Show has teamed up with Josh Adam Meyers to bring a new show to Los Angeles's stage. The Goddamn Comedy Jam consists of one part comedy show, one part rock show. Comics booked perform a set of stand up comedy, then are forced to perform a song of their choosing, unrehearsed, with a full band. With its debut just last month, Goddamn Comedy Jam returns August 18th with a killer lineup, including the return of Bill Burr.

David Koechner will headline Super Secret Comedy Show on May 7th, 2014, accompanied by an amazing lineup. Tickets are already selling and moving well. Hope to See you there, exciting things happening with the show!

The next Super Secret Comedy Show is Wednesday 4/23, with Anthony Jeselnik, Neal Brennan, Iliza Shlesinger, Steve Simone, JJ Whitehead, Josh Waldron, Jessica Keenan and hosted by Flula. Click on the photo below for Tickets!