[13] Following graduation, Crawford attended Pepperdine University, studying broadcast journalism and marketing,[12] but dropped out after a few semesters to focus on his acting career.

Long Lost Son (2006 film), In March 2007, he landed the role of main character Nate Archibald on The CW's teen drama series Gossip Girl, making his television debut.

[18] He then portrayed the lead role, a drug dealer named White Mike, in the film Twelve, directed by Joel Schumacher.

[23] In January 2014, Crawford signed on to guest star on the 100th episode of the Fox comedy-drama series Glee as Biff McIntosh, Quinn Fabray's (Dianna Agron) new boyfriend, which aired on March 18, 2014.

[25][26] In April 2014, it was reported that Crawford had landed the lead role of Jacob Martin in the psychological thriller film Eloise, directed by Robert Legato and written by Chris Borrelli.

[27] On March 11, 2015, it was reported that Crawford had been cast in ABC's primetime soap opera Blood & Oil, portraying the lead role of Billy LeFever.

[28] In 2016, Crawford played the role Arthur Barone in the independent sports comedy-drama film Undrafted, written and directed by Joe Mazzello.

Based on the true story of a promising young baseball player, the project was filmed at Dunsmore Park in La Crescenta, California.

[31] 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.

[33] 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.

[36] In January 2018, it was announced that Crawford has been cast as Kevin Moskowitz / The Deep in The Boys, the Amazon Studios adaptation of Garth Ennis and Darick Robertson's comic book of the same name.

[41] In August 2021, Crawford was announced to star alongside Nina Dobrev in ensemble comedy Reunion from director Chris Nelson.

[49] Because it did not involve a drug dealer or bag of weed, he cut a deal to pay for his marijuana possession arrest with probation and community service in 2011.