In 2014, he co-starred alongside Casey Wilson and Ken Marino in the NBC sitcom Marry Me, playing the role of Gil. On June 5, 2015, Gemberling and fellow Comedian friends Gil Ozeri and Adam Pally gained attention when they teamed with Funny or Die to live-stream their 50-hour marathon of Entourage, watching every episode in a row with no breaks for 50 hours straight.