Career Timeline of Cole Escola: Major Achievements and Milestones

Updated: July 16, 2025

From career breakthroughs to professional milestones, explore how Cole Escola made an impact.

Cole Escola is an American comedian, actor, singer, and playwright recognized for their cabaret performances and television roles in shows like *Difficult People*, *At Home with Amy Sedaris*, *Search Party*, and *Big Mouth*. Most notably, they wrote and starred in the play *Oh, Mary!*, which premiered on Broadway in 2024. Escola received two Tony Award nominations for their work on *Oh, Mary!*, ultimately winning the Tony Award for Best Actor in a Play and being named a finalist for the Pulitzer Prize for Drama.

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Full Timeline Career & Achievements

2008: Regular Performer in Our Hit Parade

From 2008, Cole Escola was a regular guest performer in the Our Hit Parade cabaret series.

2008: Met Jeffery Self

In 2008, Cole Escola met fellow comedian Jeffery Self in New York. Together, they began creating YouTube videos under the moniker "Very Good Looking (VGL) Gay Boys."

June 19, 2009: Premiere of Jeffery & Cole Casserole

On June 19, 2009, Jeffery & Cole Casserole premiered on Logo TV. It ran for two seasons.

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2012: Cabaret Shows

In 2012, Cole Escola began performing monthly solo shows at the Duplex Cabaret Theatre. They also appeared in Scott Wittman's cabaret show Jukebox Jackie at La MaMa.

2013: Present Laughter

In 2013, Cole Escola played Roland Maule in the Two River Theater revival of Noël Coward's Present Laughter.

2014: Rock Bottom at Joe's Pub

In 2014, Cole Escola played an unborn fetus in Bridget Everett's cabaret show Rock Bottom at Joe's Pub.

2015: Appearance on Difficult People

In 2015, Cole Escola appeared as Matthew on the Hulu television series Difficult People.

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June 14, 2017: Premiere of Help! I'm Stuck

On June 14, 2017, Cole Escola's hour-long solo show Help! I'm Stuck premiered at Joe's Pub, where it has since played numerous sold-out engagements.

2017: Appearance on At Home with Amy Sedaris

From 2015 to 2017, Cole Escola played Matthew on Difficult People. In 2017, they also appeared in recurring roles on At Home with Amy Sedaris, playing Sedaris' neighbor, Chassie Tucker.

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2020: Appearance on Search Party

In 2020, Cole Escola appeared as Chip (The Twink) on the HBO Max original Search Party.

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2021: Search Party Regular & What We Do in the Shadows

In 2021, Chip became a season regular in season 4 for Search Party. Escola also voiced a gargoyle in an episode of What We Do in the Shadows.

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2021: Voice Acting Roles

In 2021, Cole Escola voiced a gargoyle in an episode of What We Do in the Shadows. Chip became a season regular in season 4 of Search Party.

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2022: Appearance on Big Mouth

In 2022, Cole Escola appeared on Big Mouth.

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July 2024: Broadway Debut of Oh, Mary!

In July 2024, Oh, Mary!, written by and starring Cole Escola, transferred to Broadway, marking their Broadway debut as an actor and playwright.

2024: Broadway debut in Oh, Mary!

In 2024, Cole Escola wrote and starred in the play Oh, Mary!, which opened on Broadway. They received two Tony Award nominations for their work on Oh, Mary!.