Van Sant is one of the most overrated â€œname” directors on the planet. “My Own Private Idaho” is only good in the scenes in which Reeves and Phoenix are alone and the “director” lets their natural repressed sexuality and bond with each other unfold. The rest is wretchedly unwatchable. “Good Will Hunting” is the only good film with his name attached to it and that is primarily because of the great script and performances that he, by pure chance, was unable to smother to death as he has most everything else heâ€™s touched. People remember “To Die For” only because someone Hipper Than Thou told them they were supposed to.
If this casting is true, it is only further proof he is less auteur than autistic. Penn can act but one finds it impossible to imagine him acting his way sufficiently out of his perpetual soured beer expression to convey the joie de vivre that Milk had as well as his ability to inspire. He might work as Milk’s corpse, however.
Damon could work with a lot of effort and a hair dye job, but his â€œbaby faceâ€ would work against him. Otherwise he is HUGE box office and his last two films are the two Iâ€™ve enjoyed the most in the last year.
The average filmgoer can’t name four movies by van Sant, let alone four they actually treasure. It’s dangerous using hoi polloi as a touchstone for much of anything but many could name at least one person they’ve heard is “a great filmmaker” and the chances of that being van Sant are nil.
Another reason Penn is a horrible choice is that he is hated by Middle America as the equivalent of a modern day “Hanoi Jane [Fonda].” The unfairness of that characterization is beside the point. They, far more than the average gay person, need to see gay-affirming films and casting Penn would be just another excuse for them to stay away even if the film did turn out to be as excellent which, again, is unlikely with van Sant helming it.
Only two of Penn’s 30+ films have grossed over $50 million in the US. Even the six-Oscar nominated, two-Oscar winning, icon Clint Eastwood-directed “Mystic River” only brought in $90 million. Even including â€œMystic Riverâ€™sâ€ worldwide grosses, “Brokeback Mountain” brought in more. His last film, even with his Oscar for â€œMystic,â€ grossed less than $9.5 million worldwide which, with a production budget of $55 million, means it lost $45+ million.
Only four of Van Sant’s films have grossed more than $20 million. Whatever else one might say about the director allegedly also working on a Milk bio, Bryan Singer, three of his five films have grossed over $150 million domestically.