JACKSON: Boy I gotta tell you, did they get your description wrong.
JACKSON: Oh yeah, much more George Clooney than Brad Pitt. Hey Andrew.
JACKSON: Don’t you think he’s much more George Clooney than Brad Pitt?
ANDREW: I’m going with the Billy Crudup comparison myself.
George Clooney (born 1961) is an American award-winning actor, director, producer, screenwriter, activist, businessman, and philanthropist. He made his television debut in 1978, and found fame on the medical drama ER from 1994 to 1999. During this time he took major roles in films such as Batman and Robin (1997) and Out of Sight (1998). In 1999 he had the lead role in Three Kings, a satire about the Gulf War. Clooney is generally seen as one of the handsomest men in Hollywood.
Brad Pitt (born William Bradley Pitt in 1963) is a multi award-winning actor and producer. He first gained recognition as a cowboy hitchhiker in Thelma & Louise (1991), and had leading roles in A River Runs Through It (1992), Legends of the Fall (1994), and Interview with the Vampire (1994). He received critical acclaim for Seven (1995), and Twelve Monkeys (1995), and starred in the cult film Fight Club (1999). At the peak of his career, he was seen as one of the sexiest men in Hollywood.
William “Billy” Crudup (born 1968) [pictured] is an American actor with extensive experience on the stage, mostly on Broadway. He has had supporting roles in films such as Sleepers (1996), and Almost Famous (2000). He gained financial success narrating the “Priceless” campaign for MasterCard from 1998 to 2005. Unless it’s cut very short or slicked back, Crudup has wavy hair, which may have reminded Andrew of Christopher’s locks; he’s also from a similar upper-middle class background to Christopher, who is identified as looking as if he comes from “money”.
Which of these actors Christopher most looks like is a matter of opinion. To me he doesn’t strongly resemble any of them, but presume that the Stars Hollow townsfolk are referring to different types of masculine good looks – handsome sophisticate, sexy charmer, or preppy hipster. Christopher apparently has elements of all these in his appearance.