Ing taun 2000an, McConaughey dadi kawentar amarga mbintangi filem komedi romantis, kalebu "The Wedding Planner" (2001), "How to Lose a Guy in 10 Days" (2003), "Failure to Launch" (2006), "Fool's Gold" (2008), lan "Ghosts of Girlfriends Past" (2009). Kawit taun 2011 dhèwèké luwih seneng main ing peran dramatis, ing sawenéh filem ya iku "The Lincoln Lawyer" (2011), "Bernie" (2011), "Killer Joe" (2011), "The Paperboy" (2012), "Mud" (2012), "Magic Mike" (2012), "The Wolf of Wall Street" (2013), "Dallas Buyers Club" (2013), and "Interstellar" (2014).