Worth Full-Price, Matinee or Rental: Full price if you're looking for pure Oscar-bait material, and have a strong interest in Harvey Milk. Otherwise, a matinee would be an exceptional value.
Will I Own It On DVD: Probably not. I'm really glad I saw this film, and although it was extremely well-done and powerful, I can't imagine re-watching it enough to justify buying it. 
1) "Milk" kicked off my annual round-up of films which I assume will be up for major Oscar contention, a list that also includes "Slumdog Millionare," "The Wrestler," and "The Curious Case of Benjamin Button" (I could care less about "Doubt" and refuse to see it).
That being said, I wasn't overly excited about seeing "Milk," however, the movie turned out far better than I anticipated as it provided a striking history lesson that was anchored by a terrific performance by Sean Penn.
2) Rarely do movies get released during times when the current political or cultural landscape parallels the different era captured on film. "Milk" is an exception as it feels very relevant with the recent defeat of Proposition 8 in California as the major issue at the heart of the movie was Harvey Milk's crusade to defeat passage of Proposition 6 in California during the 1980s, a law which would have made it legal to remove people from their jobs if they were determined to be gay. 
3) Sean Penn gives a phenomenal performance as Harvey Milk. This comes as no surprise since he seems incapable of turning in a bad job, but the surprising part in this movie was Penn's ability to dial-down his usual raging intensity and channel it in an extremely understated way. The trick to his performance is that he was still absolutely riveting while restraining his typical brashness and this allowed him to disappear into the character.
4) James Franco, Josh Brolin and Emile Hirsch led a supporting cast that nearled equaled Penn. Brolin continued his hot streak (although the script never gave him much to do or delved deeply enough into his ultimately violent psyche), and Hirsch overcame a shaky opening scene to deliver a really fine performance.
But it was Franco who really grounded the film as he played Penn's on and off again boyfriend. Their relationship felt very genuine as the two actors played well off each other, and balanced out the political landscape of the film with a compelling personal angle.
I generally find Franco to be a pompous blowhard in interviews, however, he was great this year in both "Milk" and as a pothead in "Pineapple Express," so I have to give him his due credit. 
5) Gus Van Sant tells a fine story in "Milk" with a return towards his more commercial instincts (see "Good Will Hunting") versus his hard-core indie ventures (see "Elephant" or "Gerry" or don't). He paces "Milk" extremely well, pulls fine performances from his cast and builds the tension and drama so steadily that you don't notice just how powerful it becomes until the ending. The fact that it's mainly a true story only enhances the experience.
-BDS
I've heard this is Franco's big breakout role and I liked him in "Pineapple" as well. Sean Penn is just always excellent so that's a given. I don't know if I'll see it or not, but I'm sure there were some fine performances. (I'm not a homophobe. lol)
Sean Penn will always be Jeff Spicoli to me. I just can't get past it.
The documentary, The Times of Harvey Milk is a good rental for anyone who wants to know more about the man. Can't wait to see Milk. Franco does give a rather strange interview, though the press he's done lately he's been pretty good. I'll be on Oscar watch this weekend as well, good stuff coming out this week.
Jlee - No worries on that front as I felt the exact same way as you (i.e. knew it would be pretty good, good performances, etc.) and yet I wasn't that excited to see it. I'm glad I did, but it would also be fine as a rental.
Heff - Spicoli was one of the finest creations ever put onto film. It endures quite well.
Linda - I was going to watch to see if you reviewed "Milk" as I must have flown by you in Cyberspace. Thanks for the heads up on the documentary front too. This is definitely the season for good stuff coming out, so I hope you catch (and review) some of the best ones. I might catch 'Benjamin Button' depending on the Xmas anarchy.
I'm getting so sick of Sean Penn making this overly powerfyl, blatantly political films. Once and a while, throw in some romantic comedy or action movie or something. Just for diversity. Otherwise, he comes across as a preacher. And the cinema is the last place in the world that should be preaching.
I want to see this - and you're right, the timing seems pertinent.
I can't believe I haven't even seen any previews for this movie. Sounds good, I may just have to go check it out.
I of course have not seen a preview for this however I do love Sean Penn so I think I'll give it a go.
It's on my list and if this f-ing snow would clear, I could get out to the movies. Why don't you want to see "Doubt?"
We have a Christmas Day tradition of having a family breakfast, drinking one too many mimosas and then seeing a movie. Or two.
I was a little concerned about Penn doing this one because I was worried it might be more about him saying "see? I'm doing another meaningful and important role! pay attention!" While the man is a brilliant actor, it should be about the role, not about him in it. Your statement "this allowed him to disappear into the character." is the greatest possible review and alleviates my concerns.
WhatIgot - I agree about loathing preachy movies, but I can't remember Penn being in a ton of politically-motivated films outside of "All the King's Men" which was supposedly a horrible film. Maybe my memory is poor in this regard . . .
Grace - It's a smaller movie, and it's just now coming out in major cities, so you might hear more about it very soon (especially if it gets Oscar nominations). It was really good.
Native Minnow - Then you should definitely check this one out as it delivers pretty well.
Miss Ash - That's no surprise at all. Ha. And if the subject matter grabs you at all, then I would recommend it.
A.B. - I was wondering if you were still snowed under out your way as the white stuff seems to be everywhere but Austin. That sounds like a great Christmas tradition to me, so hopefully you pick a good one (or two or three . . .). As for "Doubt," I just could care less about the Catholic church, it appears that Streep might be overracting and I just don't think I would leave feeling good about anything at all. I could be very wrong. Ha.
Bostonpobble - You expressed my exact reservation about this film and Penn's role in particular far better than I could have. I was very nervous, but luckily, I felt it was a non-issue from the start of the running time. Whew.
You write a fantastic review B. Someone should snap you up to do this professionally.
I haven't even heard of this movie but I do want to see The Curious Case of Benjamin Button. I love Cate Blanchett as an actress and Brad Pitt...well what can I say?
Santa will be here in just a few hours so on that note I would just like to say merry Christmas to you and your wife and I look forward to reading more of your great posts in the coming year. Cheers!