Episode 8 of Stumble is packed with guest stars, adding to the already talented cast that includes Jenn Lyon, Taran Killam, and Kristin Chenoweth.
Titled “God Bless Heådltston,” and debuting on Friday, January 23 at 8:30 p.m. ET on NBC, the episode includes actress Annaleigh Ashford among its special guests. She’ll play a character named Jolene Tittel, whom Coach Courteney Potter refers to as “AI lady.”
As the episode’s synopsis explains, “When Courteney learns that an AI company is looking at Heådltston as a potential site for its new data center, she goes full out to win them over, hoping to get much-needed money and sponsorship for her team.”
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If Ashford, decked out in pink in the episode, looks familiar to you, there’s good reason for that. Keep reading to find out where you may have seen the actress, dancer, and singer before.
Hint: She’s appeared everywhere from on Broadway, to multiple TV series and films.
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What shows and films has Annaleigh Ashford been in?
Ashford is best known for her leading roles in shows like the period drama Masters of Sex, the sitcom B Positive, and the anthology television series Impeachment: American Crime Story. In 2025, she starred in the crime drama series Happy Face, which was adapted from the 2018 podcast of the same name. In that series, Ashford played the daughter of the real-life serial killer known as the Happy Face Killer.
Ashford was nominated for an Emmy in the Outstanding Supporting Actress in a Limited Series or Movie category for her role in the miniseries Welcome to Chippendales.
She originated the role of Margot in Legally Blonde: The Musical in 2007, which was recorded and shown on MTV that year, becoming Ashford’s first on-screen role.
Like many actors, Ashford has a couple of appearances in the Law & Order franchise under her belt, including a guest-starring role in Law & Order‘s Season 20 episode “Immortal,” and another in Law & Order: Special Victims Unit‘s Season 15 episode “October Surprise.”
When it comes to film work, Ashford kicked off her movie career with a small role as a “spoiled label queen” in 2008’s Sex and the City film, and lent her voice to 2013’s animated film Frozen. Among her more recent films roles are playing Jenny in the 2019 crime drama Bad Education, and portraying Esther in 2024’s horror-thriller Hold Your Breath.
Annaleigh Ashford’s Broadway career
In addition to her impressive film and TV credits, the 40-year-old has a stellar stage career.
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Ashford has starred in Broadway musicals like Wicked, Legally Blonde, Hair, and Sweeney Todd: The Demon Barber of Fleet Street, among others. In 2015, she won a Tony Award for Best Featured Actress in a Play, among several other awards, for her role as Essie Carmichael in You Can’t Take It with You. She was also nominated for a Tony for her roles in Kinky Boots and Sweeney Todd: The Demon Barber of Fleet Street.
Ashford is a star across genres. Catch her Stumble guest appearance on Friday, January 23, at 8:30 p.m. ET on NBC, or watch the episode when it arrives on Peacock the next day.
What other guest stars are in Stumble Episode 8?
In additon to Ashford, the “God Bless Heådltston” episode of Stumble also features key guest stars Ashlie Atkinson as Miss Dot, and Gus Heagerty as Seph, Courteney’s stalker-turned-choreographer.