I’ve been teasing my next bracket challenge for a few weeks, and it’s finally here! I originally planned on doing this bracket challenge last year when we had a nice even 96 films that had won the Oscar for Best Picture, but life got busy and I decided to wait. So now we have 97 films!
I’m planning on doing this in little chunks to make it more manageable, four pairs of films at a time (with 5 the first time because of that pesky 97th film throwing everything off). I’ll post the segment of the bracket for the week and give everyone a look at what the matchups are as well as who the winner will be facing in the next round.
And of course, don’t forget to subscribe to the newsletter to make sure you get the emails with each week’s set of matchups.
If you want to see the full bracket, check it out here.
So on to the first set of matchups!

#64 Rain Man (1988) vs # 65 A Beautiful Mind (2001)


We start off with a couple of big hitters way down in the mid-60s. I thought Rain Man would end up higher on the seedings, but once we get to some of the top half of the films, you’ll start to see why some of these good films are farther down the list. We just have such a great set of films (for the most part) that even REALLY good films get pushed down the list. A Beautiful Mind also seems like it’s seeded too low, but I did prefer Gladiator over this in terms of late 90s early 2000s Russell Crowe.
#32 Forrest Gump (1994) vs #97 The Broadway Melody (1929)


Someone had to be last, and sadly it’s The Broadway Melody from 1929. The film won Best Picture at just the Second Oscars, and I’ll be covering it on my podcast in just a few weeks with
. It will be interesting to see how well it handles good old Forrest, Forrest Gump, but given how well Forrest handled just about anything thrown in his path, I’m not sure the first “talkie” to win Best Picture stands much of a chance.#33 Million Dollar Baby (2004) vs #96 Cimarron (1931)


As with the Forrest Gump matchup above, I’m not sure if Cimarron has even a puncher’s chance at beating Million Dollar Baby, but I might be surprised. I know I watched Cimarron several years ago, but I really don’t remember much about it other than that it’s a western. Million Dollar Baby on the other hand delivers memorable performances from Swank and Freeman (who both won acting Oscars for their roles) all helmed by Eastwood’s direction.
#49 Ordinary People (1980) vs #80 Terms of Endearment (1983)


To be honest, these films are both glaring blank spots on my film history resume. I’ve never sat down and just watched some of these early 80s films, but I think I really need to now. Ordinary People was Robert Redford’s debut feature as a director and starred Donald Sutherland, Mary Tyler Moore, and Judd Hirsch while Terms of Endearment was directed by James L. Brooks (co-creator of the Mary Tyler Moore Show coincidentally) and also featured a star studded cast of Shirley MacLaine, Jack Nicholson, Danny DeVito, and John Lithgow. It’s a shame we will lose one of these classics in the first round.
#48 How Green Was My Valley (1941) vs #81 Titanic (1997)


Last up for this post is one film that probably everyone reading this has seen against a film that only a small percentage of readers has probably even heard of. Interestingly, they are both by big name directors, John Ford and James Cameron. That said, How Green Was My Valley has 372 fans and 28,000 ratings on Letterboxd while Titanic has 43,000 fans and over 2 million ratings. Will Titanic be able to stay afloat against a John Ford classic?
This is great!
This is so fun! Thanks for putting this effort together.