Born in Jonesboro and raised in Little Rock, this self-called "pretty boy" participated in sports in an effort to counteract the teasing and abuse he faced from his classmates over his countenance. Simultaneously, Bentley also acted in school plays and local competitions in what he described to Erik Himmelsbach in TIME OUT NEW YORK, September 9-16, 1999) was an effort "that was my need to prove to people that I was better than what they thought of me, or what I THOUGHT they thought of me." At his mother's suggestion, he applied for and was accepted by Juilliard where he was cast in stage productions. Roles in independent films like "Three Below Zero" (1998) soon followed as did a small part in "Beloved" (also 1998). While waiting on line at an open call for the musical "Rent", Bentley was spotted by a casting agent who asked him to read for a movie. After seven callbacks, he landed the job, although he declines to identify which film it was, merely stating "I don't know WHERE the movie is now." (VANITY FAIR, October 1999).
Bentley reportedly landed his breakthrough role in "American Beauty" despite heavy competition from more "established" names. As Ricky, a former mental patient whose overbearing father (Chris Cooper) pressures him with drug tests and a vituperative tongue, the young actor offered a nuanced portrait of a disaffected teenager. Only when he finds a kindred soul in his neighbor Jane (Thora Birch) does he find some kind of hope and the pair delivered fine performances that encompassed both the humor and the drama of the piece. Before he was even able to reap the benefits of his sterling reviews, Bentley had completed "The White River Kid" (Starz!, 2000), playing a young serial killer who crosses paths with an itinerant con man (Antonio Banderas). He went on to portray a railroad surveyor in "The Claim" (2000), Michael Winterbottom's intriguing resetting of Thomas Hardy's "The Mayor of Castorbridge" to 1860s California and was cast alongside Eliza Dushku and Luke Wilson in the thriller "Soul Survivors" (2001).