Following graduation from
Wright State University, his first acting job was a recurring role on
L.A. Law as Ned Barron, which lasted for six episodes from 1991 to 1992. Sherwood was introduced to improv after being encouraged to attend a comedy class in Los Angeles, In 1992, Sherwood appeared in two episodes of the fourth season of the British
improvisational comedy television show
Whose Line Is It Anyway?. He was the only actor from that year's Los Angeles auditions to make it to the cast. In 1997 he returned to the show, becoming a regular performer during the last two seasons. He then joined the American version of
Whose Line Is It Anyway? which began after the British version ended and originally aired on the American broadcaster
ABC. The American version was hosted by comedian
Drew Carey. Sherwood later made a guest appearance in three episodes of Carey's sitcom
The Drew Carey Show. He was also a producer and performer on ''
Drew Carey's Green Screen Show (2005) and a performer on Drew Carey's Improv-A-Ganza'' (2011). In 2013, the American broadcast network
The CW revived
Whose Line?, on which Sherwood has made occasional appearances. Sherwood hosted
The Dating Game from 1996 to 1997 and
The Big Moment in 1999, and was a guest host on
Talk Soup. He has also been a regular panelist on
To Tell the Truth,
Jury Duty, and
Hollywood Squares. He regularly appears on numerous
VH-1 series, including
I Love the 70s,
I Love the 80s,
I Love the 90s,
100 One-Hit Wonders of The 80s,
100 Greatest Rock Ballads,
I Love Toys, and
Greatest Game Show Moments. He was a guest on
Larry King Live and a regular panelist on
Chelsea Lately. ==Filmography==