Pope started comedy at the age of 28 at the suggestion of one of his brothers.[2][3] He adopted the surname "Pope" as his stage name to avoid being confused with comedian Tom Papa.[1]
In 2011, he won "Philly's Phunniest", a yearly comedy contest held by Helium Comedy Club, and was featured in the "New Faces" showcase at the Just for Laughs festival in Montreal the following year.[4] He made his television debut on AXS TV's stand up series Gotham Comedy Live in 2013 and was a contestant in the eighth season of NBC's Last Comic Standing in 2014.[5][6]
Pope first met frequent collaborator, John McKeever (co-creator and director of the web series Gilly & Keeves with comedian Shane Gillis) in 2008 while performing stand-up comedy at The Raven Lounge in Philadelphia.[1][7] Pope, McKeever and Luke Cunningham (writer for The Tonight Show Starring Jimmy Fallon) formed comedy sketch group BirdText from 2010 to 2014.[1][8] The group performed a monthly show at Helium Comedy Club and also produced digital content which has been featured on VH1, NPR's Fresh Air, Philadelphia Magazine and National Lampoon.[4] They became known for their video series Real Househusbands of Philadelphia, a spoof of the Real Housewives franchise.[1][9] In 2013 Pope appeared in a sketch featuring Steve Martin on The Tonight Show Starring Jimmy Fallon.[10] Cunningham was writing for the show at the time.[10]
In 2014 Pope and McKeever created another comedy sketch group, Deer Prom, that performed regularly at Carolines on Broadway and they performed at the New York Comedy Festival in 2014.[1][11] As Deer Prom, Pope, McKeever and comedian Tim Butterly created the comedy series Delco Proper for Comedy Central.[12] The series revolves around the lives of three best friends from Philadelphia and Delaware County and the network initially posted a single episode to their website in 2015, followed by three more episodes in 2016.[9][12] In 2017 Comedy Central announced that it had ordered Delco Proper for their 2017–2018 season, however the show did not make it to air on their television network.[12]
Pope was featured in an episode of the Comedy Central storytelling series, This Is Not Happening, in 2018.[13]
In 2021, Pope and fellow comedian Chris O'Connor, who share a New York apartment, started the podcast Stuff Island.[14] The podcast features conversations with a different comedian each episode, recorded from their living room.[14]
