America, and soon the universe, fell head over heels for Leonardo DiCaprio in 1998. The baby-faced, debonair actor stole everyone’s hearts as Jack Dawson, Titanic‘s manic pixie dream guy. Leo was no stranger to critical acclaim even before his role as Jack: Audiences loved him as the titular Marvin in Marvin’s Room  and Johnny Depp’s younger brother, Arnie, in What’s Eating Gilbert Grape? The tragic heartthrob role felt tailor-made for Leo, especially as he downed the poison in Claire Danes’ arms during Baz Luhrmann’s remake of Romeo & Juliet. Then, the mood shifted: Leo’s characters underwent a subtle transformation from kind-hearted dream guys to manipulative, egomaniacal villains, at worst or anti-villains, at best. Case in point, Leo wanted to shake off the lover-boy image he created via Jack Dawson by starring as Richard in The Beach, which was utter box office drek. Not only was the premise risible, Leo’s character steals another guy’s girlfriend, cheats on her, then repeatedly gaslights fellow members of his commune in Thailand. The Aviator puts Leo in the shoes of Howard Hughes, the greedy, philandering oil tycoon and wannabe movie director. The guy crashes planes for the sheer fun of it; demands a cloudy sky where there isn’t any; cheats on Katharine Hepburn with a string of gals and guys (notably Cary Grant!), and drags everyone into his self-inflicted paranoid bubble… and he crashes his plane into a series of homes, killing their respective residents. The Man in the Iron Mask  features Leo as King Louis XVI. (We all know how the monarch’s fate played out.) Catch Me If You Can is a heart-pounding caper biopic about Frank Abagnale, Jr, whose criminal career has the Freudian rationalization of being a scapegoat for his mother’s philandering and subsequent divorce from his father. Frank becomes a true antihero, as he redeems himself by becoming an FBI informant. Speaking of informants, The Departed (a remake of Infernal Affairs) features Leo as Billy Costigan, a Bostonian mole. Revolutionary Road reunites Leo with Kate Winslet (his offscreen BFF for over twenty years) as husband and wife. Leo’s character, Frank, oozes toxic machismo, which drives his wife to suicide. The abusive husband trope continues to follow DiCaprio for the next several roles: He distorts his wife Mal’s reality in Inception by literally mind-raping her to the point that she denies the real world’s existence and jumps out the window. Shutter Island presents Teddy Daniels, who investigates the disappearance of a patient from a remote mental facility. We later discover that Teddy Daniels is really the lobotomized alter-ego of one Andrew Laeddis, who drowned his wife and subsequently developed a dissociative personality disorder. Who could forget The Wolf of Wall Street? DiCaprio deserved every bit of acclaim for his portrayal of the smug-snake stockbroker, Jordan Belfort. Unlike Frank Abagnale, Belfort has zero redeemable qualities: He swindles innocent people out of money (the penny stock version of Bernie Madoff, basically), trades his loving, compassionate brunette wife for a piece of blonde arm candy, later kidnaps his and arm candy’s daughter, refuses to leave his post at Wall Street and make amends with former clients, and resumes his role as a corporate Svengali with the “sell me this pen” schtick, which started his career. Luckily, his portrayal of Hugh Glass in The Revenant brought back the Leonardo we all know and love.