Crawford made his film debut in the 2006 supernatural horror-thrillerThe Covenant, as Tyler Simms. Long Lost Son (2006 film), In March 2007, he landed the role of main characterNate Archibald onThe CW's teen drama seriesGossip Girl, making his television debut.[15] In 2008, Crawford co-starred in the crime-thrillerLoaded, and portrayed the lead role in the supernatural horror filmThe Haunting of Molly Hartley. The following year, he played English singer-songwriterLeona Lewis' boyfriend in the video for her single "I Will Be", which was released in January 2009.[16] That same year, Crawford was named "Summer's Hottest Bachelor" byPeople.[17]
In January 2014, Crawford signed on to guest-star on the100th episode of theFox comedy-drama seriesGlee as Biff McIntosh,Quinn Fabray's (Dianna Agron) new boyfriend, which aired on March 18, 2014.[24] In March 2014, Crawford landed the lead role of Cooper Pollard in the independent comedyMountain Men. The film follows two brothers who do not get along as they take a trip to the mountain to look for their missing father, however they get stuck there and have no other choice but to work together to get back home. The film co-starsTyler Labine.[25][26]
In April 2014, it was reported that Crawford had landed the lead role of Jacob Martin in the psychological thriller filmEloise, directed byRobert Legato and written by Chris Borrelli. The film is about four friends who break into an asylum so Jacob could get an inheritance of the death certificate. Once inside the asylum, they discover the truth about their tragic past. It also starsEliza Dushku,Brandon T. Jackson, andPJ Byrne.[27] On March 11, 2015, it was reported that Crawford had been cast inABC's primetime soap operaBlood & Oil, portraying the lead role of Billy LeFever. The series was cancelled after a short run of 10 episodes.[28]
In 2016, Crawford played the role Arthur Barone in the independent sports comedy-drama filmUndrafted, written and directed byJoe Mazzello. Based on the true story of a promising young baseball player, the project was filmed at Dunsmore Park inLa Crescenta, California.[29][30] Also that year, he had a minor role in the filmRules Don't Apply, written and directed byWarren Beatty.[31]
Crawford in 2012
In April 2016, it was announced that Crawford had landed the role of Egon in the comedy filmI Do...Until I Don't oppositeAmber Heard andEd Helms.[32] The film was written and directed byLake Bell.[33] In the same month, it was reported byTheWrap that he would perform in a live-reading of theBlack List scriptCollege Republicans, portraying the role ofJohn F. Kinney. The reading took place at the Montalban Theater on April 23, 2016.[34] In March 2017, it was announced that Crawford had joined the cast of the comedy showCasual in the recurring role of Byron.[35] The same year, he signed on to star in the crime movieRiptide as Landen and comedy filmAll About Nina as Joe.[36]
In August 2021, Crawford was announced to star alongsideNina Dobrev in ensemble comedyReunion from director Chris Nelson.[42] On October 9, Crawford did an uncredited cameo on aSaturday Night Live episode in aThe Bachelorette parody skit.[43] In December, Crawford was announced to voice act in the English-language version ofMamoru Hosoda's 2021sci-fianime,Belle. It was released the following month alongside the Japanese-language version on January 14, 2022.[44] In February 2022, it was announced that Crawford would develop afootball drama atShowtime, alongside formerDallas Cowboys quarterbackTony Romo, who is also Crawford's brother-in-law, andYellowjackets executive producer Drew Comins.[45] In March 2022, Crawford reprised the role of hisThe Boys character, Kevin Moskowitz/The Deep, in the fifth episode of itsadult animated anthology spin-off,The Boys Presents: Diabolical.[46]
Crawford shared an apartment with hisGossip Girl co-starEd Westwick inChelsea, Manhattan, at the beginning of the series in 2007 until July 2009, when Crawford moved out to rent an apartment in theWall Street area.[47][48] In 2010, Crawford was arrested inPlano, Texas, for possession ofmarijuana.[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.[50] Crawford's brother in-law is formerDallas Cowboys quarterbackTony Romo.[51] He practicesTranscendental Meditation, which he says is like "a naturalXanax".[52]