Bentley was born in Jonesboro, Arkansas, the son of Cherie Baker and David Bentley. His father is a minister and his mother is a chaplain andordained elder in the Arkansas Conference, both in the United Methodist denomination. In 1996, he graduated from Sylvan Hills High School in Sherwood, Arkansas. Bentley attended the Juilliard School's Drama Division (Group 29: 1996–2000) but left the school after one year to pursue his acting career.
Bentley was married to actress Jennifer Quanz from 2001 to 2009. They separated in 2006 due to his substance abuse. He married producer Jacqui Swedberg in 2010 and they have a son, Charles, born in late 2010.
In a New York Times article on February 8, 2010, he described his descent into drug addiction that began almost immediately after his success in American Beauty. He said he hid his addiction from his wife; they separated in 2006, and he moved to an apartment where he began doing drugs full-time. During this time he worked sporadically, just enough to pay bills and buy drugs, and in 2008 was arrested and ordered into counseling and 12-step programs. He relapsed, however, and "continued using heroin until he was broke".
In July 2009, he said, he confessed to a friend, "I’m a drug addict, and an alcoholic, and I need help. I need help or I’m going to die". He again entered a 12-step program and, while clean since then, considers himself on the path to recovery.
The documentary My Big Break (2009) captures Bentley's early life as an unknown actor, his explosive career launch after American Beauty, his subsequent emotional struggle with fame, and his admission years later that he was recovering from an addiction to drugs and alcohol. He began to rebuild his career by starring in the Off-Broadway premier of the play Venus in Fur by David Ives.
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