In 2000, she appeared in Eat the Runt, a comedy by Avery Crozier about a job applicant's series of bizarre interviews at an art museum. During this production, by Mefisto Theater Company at Altered Stages, the actors had to be prepared to play every role in the play and, before each show, the audience drew tickets which determined what actors play which characters. The New York Times reviewer Lawrence Van Gelder said the gimmick was novel, but in the end, "the cast has probably had more sustained fun than the audience".[4]
In the summer of 2001, Williamson again appeared in Eat the Runt at The American Place Theatre, this time without the constant role switching. She played a second applicant trying to get the museum job, who claims the protagonist is actually her scorned love interest who is only pretending to seek the job in order to hurt her chances.[5][6]
In the summer of 2002, she appeared in an Off Broadway production of Hunt Holman's Spanish Girl at the Second Stage Theatre. The show was about a college student who had a summer fling relationship with a 15-year-old girl, then tries to end it. Williamson played Jolene, the strong-willed college girlfriend of the protagonist, who does not know about his affair.[7]New York Daily News writer Robert Dominguez praised her "strong performance".[8] Marjorie Gunner of New York Voice called Williamson a scene-stealer, and said she played the role "like the center of gravity".[9]
Williamson appeared in Debbie Does Dallas: The Musical, the Off Broadwaystage musical adaption of the 1978 pornographic film Debbie Does Dallas, which was shown at the Jane Street Theater starting October 2002. She played Roberta, one of Debbie's attractive young friends who perform sexual services for money.[10] Williamson, along with other female members of the cast, was praised by The New York Times theater critic Bruce Weber as "for lack of a better word, adorable", and appeared to be "having great fun while they wait for better jobs".[11] During the show, she performed a sexually-themed duet called "Make That Candle Work for You", in which Roberta and her boss sing at the candle store where Roberta works. During the song, girls dance with candles shaped like erect penises.[12][13] The song was sung by Williamson in the Debbie Does Dallas Original Cast Recording, which was released on compact disc in 2003. Her singing voice, along with those of the rest of the cast, was praised in a Los Angeles Times review.[14]
From October to November 2003, Williamson played the title role in Sylvia, a comedy by A. R. Gurney, at Playhouse on the Green in Bridgeport, Connecticut. The show was about a dog (played by a human) named Sylvia who is adopted by a couple, which creates drama in their relationship. Irene Backalenick of the Connecticut Post said of Williamson's performance, "Jama Williamson is just not doggy enough, playing it more like a petulant teen-ager. She is really convincing as Sylvia the dog only when she lies down, putting her chin on Greg's knee."[15]
Starting in October 2006, Williamson played Bella Holland, the office assistant and mistress of a married man, in a production of Simon Mendes da Costa's play Losing Louis, which played at the Manhattan Theatre Club.[16][17] The show opened with a controversial scene in which the protagonist performs oral sex on Williamson's character while his six-year-old son hides under the bed.[18][19] The show received largely negative reviews,[20][21][22] Williamson herself received mixed critiques. The New York Times writer Charles Isherwood said Williamson was one of the stronger cast members, but added, "the actors cannot do much to freshen the coarse innuendoes or breathe life into the plot contrivances".[23] Elysa Gardner, of USA Today, said Williamson added "dynamic support" to the show.[24]North Jersey Media Group critic Robert Feldberg, who was critical of the show, said her performance was amateurish and reminded him of "middling community theater." However, Feldberg said other more experienced actors were similarly bad in the show, so Williamson's faults can be blamed in part on the director.[25]Backstage said Williamson and other cast members "fail to register in any credible way".[26]
Starting in the mid-2000s, Williamson began appearing more frequently in television. In 2005, Williamson was cast as one of the three leads in a CBS Paramount Network Television pilot for the sitcom Three, in which she played Annie, the wife of a character played by James Van Der Beek. The show revolved around the happily married couple and their recently divorced male friend, played by Zachary Levi. The pilot was never sold.[3][29]
In early 2007, Williamson gave an appearance in a pilot episode of the sitcom Rules of Engagement. Although the series was picked up by CBS, the episode featuring Williamson never aired.[30]
Williamson appeared in "Democracy", a third season episode of the CBS drama series Numb3rs, which originally aired on March 9, 2007. In the episode, she played Jane Aliano, a woman who gets kidnapped as the result of a voter fraud conspiracy that led to a series of murders throughout the episode.[31]
Starting in May 2009, Williamson began making regular appearances in the NBC comedy series Parks and Recreation as Wendy Haverford, the wife of regular character Tom Haverford, played by Aziz Ansari.[32] Wendy is an attractive and well-liked surgeon, and many in the show wonder why she is interested in the sarcastic and overeager Tom. It is eventually revealed the two characters have a green card marriage to prevent Wendy from being deported to Canada.[33][34] Williamson first appeared in the first season finale "Rock Show", but made regular appearances throughout the second season. Wendy and Tom amicably separate after the December 2009 episode "Tom's Divorce",[35] but she continued to make appearances afterward.[36][37]
Williamson portrayed Nora, the mother of Loren Tate (Brittany Underwood), on the 2012 TeenNick series Hollywood Heights. In 2016, she played the recurring role of Principal Mullins on the Nickelodeon comedy series School of Rock; her role was upped to series regular for the series' second season.[38]
Williamson had a recurring role on NBC's The Good Place (2016-2020), playing Val, an actress/secretary aligned with "The Bad Place" demons led by her boss Shawn.[citation needed]
^ abAndreeva, Nellie (April 21, 2005). "Van Oy and Dunn get a 'Life' at ABC; Bateman in 'Show'; Pilot Watch". Back Stage West. 12 (17): 12. ISSN1531-572X.
^"Primetime network television". Ross Reports Television & Film. 59 (1): 46–55. January 1, 2007. ISSN1520-7722.
^"Charlie suspects that a series of murders are tied to a voter fraud conspiracy, on a rebroadcast of "Numb3rs," Friday, July 27" (Press release). CBS. July 27, 2007.