Reid began performing stand up comedy while a student at Goldsmiths, University of London in the UK . He returned to Boston in 2003 and became a regular performer at The Comedy Studio in Cambridge, MA.
Reid was a member of comedy troupe "The Untrainables", a group of stand up performers who formed around The Walsh Brothers' "Great and Secret" comedy show at ImprovBoston.

He has performed and presented at the 2006 Boston Music Awards, was the Comic in Residence at the Comedy Studio in September 2006, appeared several times in the Women in Comedy Festival, performed in the 2009 Charleston Comedy Festival, the 2009 AltCom Festival, the 2010, 2011 and 2013 Eugene Mirman Comedy Festivals, the 2013 Boston Edition of the Eugene Mirman Comedy Festival, the 2013 Bridgetown Comedy Festival, The inaugural Nines music festival in 2013, the inaugural Riot LA festival in 2012 and the second Riot LA festival in 2014.

From September 2008 to December 2012 Reid was the regular Friday night host at The Comedy Studio. In January 2013 Reid took over Thursday nights at the Comedy Studio from Sean Sullivan. Reid's show "Ken Reid's Secret Menu" ran every Thursday in 2013 at the Comedy Studio.

Reid has performed four one man shows, "Cusack Attack", "Very Special Episode", "Music to My Years" and "Shirt Tales". In September 2010 Reid performed "Very Special Episode" at the UCB Theater in New York.
He has toured with Todd Barry, and been the opening act for Patton Oswalt, Bob Saget, John Oliver, Jen Kirkman, Kevin McDonald, Kumail Nanjiani, Jonah Ray and Eugene Mirman. In May 2012 he also performed as part of a special performance of John Wesley Harding's Cabinet of Wonders variety show at Brown University called the "Cabinet of Unspeakable Wonders"

He was featured in a photo spread for The Improper Bostonian magazine in their June 2009 Sex and Love issue recreating the iconic Marilyn Monroe final photo shoot.

In 2009 he was featured in an ad campaign for jokes.com that ran on Comedy Central.

In September 2009 Reid was featured in Time Out New York as their "Joke of the Week". 

In 2010 and 2012 he was nominated by The Boston Phoenix as Best Comedian in Boston. In 2013 he was named "One of Boston's Best Comics and Stand Up Comedians" by CBS 4 Boston.

Reid is known for his story telling, and he has appeared on The Moth, Risk!, Mortified, and Stripped Stories. He is also the creator of "The Damaged Goods Auction" a story telling show in which performers tell stories about objects from their lives and then actually auction the object off to the audience.

Reid is also a frequent podcast guest and has appeared on Hang Out with Me with Myq Kaplan, Competitive Erotic Fan Fiction on the Nerdist, Put Your Hands Together, You're the Expert and Risk.

Author of "Hang the DJ" available on lulu.com. as well as amazon.com. Lead character of Santa in "Infinite Santa 8000", appears in documentary "We want the Airwaves: The WFNX Story"

Followers of wymer