In April 2016, it was announced that Crawford had landed the role of Egon in the comedy film I Do. . . Until I Don't opposite Amber Heard and Ed Helms. The film was written and directed by Lake Bell. In the same month, it was reported by TheWrap that he would perform in a live-reading of the Black List script College Republicans, portraying the role of John F. Kinney. The reading took place at the Montalban Theater on April 23, 2016. In March 2017, it was announced that Crawford had joined the cast of the comedy show Casual in the recurring role of Byron. The same year, he signed on to star in the crime movie Riptide as Landen, a drama thriller film by Grant S. Johnson called Nighthawks opposite actor Kevin Zegers and Janet Montgomery, and comedy film All About Nina as Joe.
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