Westport Country Playhouse presents singer, songwriter, and “Saturday Night Live” alumna Ana Gasteyer on August 8

Ana Gasteyer to perform at Westport Country Playhouse in Westport, Connecticut in August 2025
Ana Gasteyer – Photo by Shervin Lainez

Westport Country Playhouse will present Ana Gasteyer, singer, songwriter, and “Saturday Night Live” alumna, on Friday, August 8, at 8 p.m. She will perform songs from throughout her career – jazz standards, Broadway classics – along with comedic stories.

Ana Gasteyer is perhaps best known for her incomparable work on “Saturday Night Live.” During her six-year stint, she created some of the most iconic “SNL” characters, including middle school music teacher Bobbie Moughan-Culp, NPR radio host Margaret Jo, Lilith Fair poetess Cinder Calhoun, as well as spot-on impressions of Martha Stewart, Celine Dion, and Hillary Rodham Clinton. Additionally, Gasteyer headlined the NBC comedy series, “American Auto.”

Gasteyer is also a highly accomplished singer and songwriter. She previously embarked on a Christmas tour in support of  “Sugar and Booze,” her album of seasonal favorites and holiday originals which topped numerous “Best Holiday Album” lists. Gasteyer’s first album, “I’m Hip,” received equally rapturous reviews. She has toured around the country with her “Happy Jazz” act since 2016 and had a two-week residency at the famed Cafe Carlyle of which Stephen Holden of the The New York Times raved about Gasteyer’s comedic stories and her “strong singing voice that can stir up a storm.”

On stage, Gasteyer has starred on Broadway in “Wicked,” as Elphaba, “The Rocky Horror Show,” and Tony-nominated shows “The Royal Family” and “Three Penny Opera,” and originated the role of Debra in David Lindsay-Abaire’s “Kimberly Akimbo.” She also starred in “Funny Girl” and “Passion” at Chicago Shakespeare Theater, which earned her a Jefferson Award nomination.  At City Center Encores, she played the role of Mimi in “A New Brain,” opposite Jonathan Groff. At the Hollywood Bowl, she wowed as Miss Hannigan in the Tony Award-winning musical “Annie,” with the LA Philharmonic. Prior to joining “SNL,” Gasteyer attended Northwestern University and honed her comedy skills at The Groundlings, the famed Los Angeles improv-sketch comedy group.

Tickets are $95, $115, $125. For full details, visit: https://www.westportplayhouse.org/show/ana-gasteyer/