As Vincent Chase, the skirt-chasing superstar on HBO’s enduring bro-com Entourage, Adrian Grenier cuts the kind of swath through Hollywood pioneered by Warren Beatty, the original sexual firestarter. But the bond between these two symbols of success extends far past the reach of dark, tousled hair and shirts open to the waist.

James Dean and James Franco share a common given name, and Prince James played King James in a biopic that won Franco a Golden Globe in 2002. The two are now linked forever, but fate dove in before the agents ever placed a call. It was a casting choice far bigger than the triumph of comparable facial features and skin tone: Franco was the right person to star in that portrait because, like Dean, he is too complex, too aggressively artistic to be contained by an 8x10 glossy.