The same could certainly not be said for the gritty drama "Sleepers” (1996), in which Renfro played the young incarnation of Brad Pitt's character Michael, one of several teens savagely abused at the hands of a sadistic guard (Kevin Bacon) while in juvenile detention. A starring role as a young Hungarian immigrant boy who apprentices himself to a payola-driven radio DJ paired him again with Bacon the following year in Guy Ferland's acclaimed "Telling Lies in America” (1997). Renfro's twisted turn in "Apt Pupil" (1998) featured him as a schoolboy whose obsession with Nazism and discovery that his elderly neighbor Kurt Dussander (Ian McKellen) was, in fact, a concentration camp guard living undetected. Through blackmail, the youngster forces the older man to relate his brutal first-hand tales of the Holocaust, leading to the two developing a mutually predatory relationship. Both Renfro and McKellen were particularly chilling as the crafty manipulators in Bryan Singer's adaptation of the Stephen King novella.
While at one point the darling of the young teen set – due in no small part to his brooding good looks and cool self-confidence – of his six films released in the 1990s, only "Tom and Huck" and "The Cure" catered to that particular fan base. Meanwhile, his penchant for adult material and atypical role choices continued through his career. He delivered a powerful performance as a troubled Florida youth who turns on his abusive best friend in "Bully" (2001), directed by Larry Clark; then played it cool as a convenience store clerk uninterested in two offbeat high school grads (Thora Birch and Scarlett Johansson) in “Ghost World” (2001). After taking his first teen comedy role in the odd and decidedly dark "Happy Campers" (2002), Renfro co-starred in "Skipped Parts" (2001), a 1960s-set story of a misfit mother and her teenage son banished to a remote town by the woman's rich and overbearing father. He then had a featured turn in "Tart" (2002), a period drama following the fast-living 1980s exploits of a group of Upper East Side teens. Renfro followed with a starkly comic performance as a leader of a Brooklyn street gang in the otherwise lame “Deuces Wild” (2002).
Despite a fast rise to the top and a promising career heading into adulthood, Renfro suffered from a series of legal problems stemming from drug and alcohol addiction that frittered away his career. In June 1998, Renfro was arrested in Knox County, TN on suspicion of marijuana and cocaine possession. He later entered no plea after agreeing to submit to random drug screens in exchange for prosecutors declining to pursue charges. While he managed to stay clean for a spell, he landed in more hot water in August 2000 after getting arrested for grand theft and criminal mischief – he had tried to steal a yacht valued at over $175,000 in Fort Lauderdale, FL while on location shooting “Bully.” Renfro was released on $10,000 bond, was later sentenced to two years probation, and forced to pay the owner over $4000 in damages. Then in March 2001, he was arrested in his hometown of Knoxville for underage drinking, but managed to avoid serving jail time for violating probation because officials said that he tested negative for drugs and alcohol.
The actor was in trouble less than a year later after getting arrested for driving without a license and public intoxication in Knoxville, TN – a violation of his probation. After turning himself over to authorities, Renfro was jailed by a Broward Circuit judge, then later ordered to complete a three-month substance abuse program. The actor stayed out of trouble for the next few years, while managing to get his career back on track a bit. After a starring role in the straight-to-video action thriller “The Job” (2003), Renfro had a supporting role as the mysterious Stranger in “The Jacket” (2005), a supernatural thriller about a Gulf War veteran (Adrien Brody) whose mind is propelled into the future while his body is confined to a mental institution. But just as things were starting to look up for Renfro, the actor was in trouble again. On Dec. 22, 2005, he was arrested in downtown Los Angeles, CA in a sting operation for allegedly trying to buy heroin on Skid Row. He later pled guilty and was again sentenced to enter a drug treatment program. After appearing in “10th and Wolf” (2006), Renfro fell off the radar, only to reemerge on Jan. 15, 2008 when it was reported that the actor had died from an accidental heroin overdose in his Los Angeles home. The tragic star had been filming “The Informers” with Billy Bob Thornton and Winona Ryder. He was 25.