Benjamin Siegel, who hated his nickname to his dying day, was in many ways not your typical gangster. For one, while most gangsters cared about money, and counted every penny, he was extremely careless with it. Also, most gangsters at the time shunned the spotlight, but Bugsy loved it; not only was he involved with Virginia Hill (a bit actress), but he was friends with George Raft, and even made a screen test, wanting to be a star. And while gangsters of course made their names killing people, they mostly did it over "business" reasons, whereas Bugsy, unless he was under orders, would often do it over a psychotic rage, like if someone crossed him, or called him "Bugsy." Finally, the opposite was true as well; while it's true power, money, and even venality are great aphrodisiacs, it's said Siegel had a genuinely winning personality, and if all you did was shine his shoes, he could be the nicest guy to you.
Levinson, Toback, and star Warren Beatty certainly embrace all of these contradictions and more. They give us a clear picture of the film's tone when we first see Siegel getting a ride and doing diction exercises ("Twenty-two dwarves took turns doing handstands on the carpet"). This is a man who cares about image, so it's not surprising when in a later scene, after he's been in Hollywood awhile and made the papers quite a few times, he gently asks a photographer if he'd ask his newspaper to run a different photo than his mug shot. The best scene in the movie - the one that embraces all the contradictions - is when Siegel, getting a ride from Raft (Joe Mantegna), has him stop in front of a famous opera singer's house because, on impulse, he wants to buy it. The opera singer, naturally, is quite nonplussed, even at Siegel's hero-worship (he says he and his wife Esta (Wendy Phillips) loved his performance), and especially when he makes the mistake of calling him Bugsy (after Siegel goes off on a rant as to why he hates the nickname, the opera singer apologizes "I meant no disrespect, Mr. Siegel..." "Ben"). We seem him both charming and psychotic, and Beatty is able to be equally convincing at both, sometimes at once (as when he later savagely beats up a fellow gangster, but checks himself in the mirror while doing so).
