Taylor co-created and co-starred in Creation Nation: A Live Talk Show with Billy Eichner, which they performed at the 2008 Edinburgh Festival Fringe, as well as at the HBOAspen Comedy Festival and throughout New York City and Los Angeles. He has also appeared onstage in Neighborhood 3: Requisition of Doom, The Shooting Stage,[6]Henry IV and No. 11 Blue and White, as well as numerous productions in Stephen Sondheim's Young Playwrights Festival at the Cherry Lane Theater.[7]
Taylor was cast as Oswald Cobblepot in February 2014.[8][9] His performance as Cobblepot has been described by Esquire as a "standout performance of the first episode [...], disarming and multilayered",[10] by The Wall Street Journal as "a passionate performance ... [that] steals the show",[11] and as "spectacularly cast as the Penguin".[12]
In February 2019, it was announced that Taylor had been cast in the recurring role of Will Bettelheim on the second season of the Netflix thriller series You.[13][14]
From 2021 to 2022, Taylor also appeared in Kevin Can F**k Himself in the recurring role of Nick, a restaurant worker, across both seasons of the show.[15]
In a November 2014 Glamour interview, Taylor was asked, "I notice you are wearing a wedding ring on your ring finger. Are you married?" To which he responded, "I am married! I like to keep it private, but I've been married for over three years, and we've been together for 10½ years. No kids. No kids yet!"[17]
In March 2015, Slate noted Taylor in an article discussing "Several actors who are openly gay or who have been cast in multiple straight or bisexual roles and the typecasting of gay roles". Taylor, himself, added: "I feel like the landscape has totally changed. Regardless of sexual preference, it's more that as a character actor, the less I reveal about myself, the better. My favorite actors are the ones I know least about."[18] In April 2015, Taylor openly identified as gay on episode 672 of The Nerdist Podcast with Chris Hardwick.[19][20] In honor of National Coming Out Day in October 2019, Taylor revealed on Instagram that he had been out as gay for 22 years and encouraged followers to donate to the non-profit Rainbow Railroad.[21]