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Riley is a comedy actor and writer. He can be seen in his recurring role as Vacation Jason on truTV's The Chris Gethard Show. Riley has been performing at UCB since 2009 on Harold Night, Cage Match, Sketch Cram and in his sketch show, Vacation Jason's Island Flavors. In 2016, Riley wrote, produced and was featured in UCBcomedy's digital series, The Drawing Man Presents... Riley can also be seen in web videos for Above Average, HarperCollins, Comedy Central, TheFlama, The New Yorker, UCBcomedy.com, and in TV commercials for MTV, Boost Mobile, and Curve cologne.