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* AwesomeMusic: "Ten Million Slaves" by Otis Taylor, used in the trailer and two different scenes in the movie itself (Purvis chasing down Pretty Boy Floyd and during Dillinger's second bank robbery).
* EnsembleDarkhorse: Billy Crudup's performance as J. Edgar Hoover was praised even by people who didn't like the movie.
* HilariousInHindsight: Many a reference is made to Al Capone, who Stephen Graham (Baby Face Nelson) would go on to play in ''Series/BoardwalkEmpire''.
* GeniusBonus / HistoricalInJoke:
** When being taken into custody, Makley and Pierpont say they are being "Shanghaied to Ohio". This makes sense if you know the real reason why they were sent to Ohio to stand trial. Makley, Pierpont, and Russell Clark walked into the Allen County Jail in Lima, Ohio on October 12, 1933 to break Dillinger out of jail. In the process, Pierpont shot and killed the sheriff, Jess Sarber. Pierpont, Makley and Clark were put on trial and convicted in March 1934.
** Karpis tells Dillinger about how he and the Barker brothers Fred and Dock are planning on kidnapping a St. Paul banker named Edward Bremer, with Dillinger turning down the offer. Though Karpis may never have actually met Dillinger, his gang did go through with the Bremer kidnapping on January 17, 1934 - two days after Dillinger and Hamilton robbed a bank in East Chicago, Indiana.
** There's also a mention during the same scene where the Dillinger gang members mention Karpis's previous major crime - the kidnapping of William Hamm in June 1933 around the time of the Kansas City Massacre.
* HollywoodHomely: Billie's alleged "$3 dress" (around $50, adjusted for inflation) doesn't exactly look cheap by today's standards.
* JerkassWoobie: John Dillinger, definitely during his humane moments. Witnessing Billie Frechette taken away in handcuffs in particular, and crying as he drives away unnoticed. He was so distraught by Billie's arrest that he considered intending to rescue her while she was being transported to St. Paul to stand trial, which everyone else in the gang - John Hamilton, Baby Face Nelson, Homer Van Meter and Tommy Carroll all were against. Van Meter, however, did know where they could get vests. Indeed, that Friday morning, a few days after Billie was arrested, Dillinger and Van Meter went to Warsaw, Indiana, where they took a police officer, Judd Pittenger, hostage (there was a brief struggle where Pittenger tried grabbing the barrel on Dillinger's Thompson, and Pittenger was then pistol-whipped by Van Meter) and walked him to the police station armory at gunpoint, where they took a number of pistols and bulletproof vests.
%%* MagnificentBastard: John Dillinger.
* TearJerker: Dillinger's death scene is also surprisingly accurate, and is surprisingly good at making the audience feel sympathetic for him before he dies.
%%* ValuesDissonance: It's the 30s, natch.