10. Thirteen Days (2000)
The true story of the Cuban Missile Crisis is compelling viewing, even though we all know how the story ended. That’s the true mark of compelling drama. Costner plays Kenneth O’Donnell, an advisor of JFK through this heart-stopping crisis.
9. Robin Hood: Prince of Thieves (1991)
Costner’s take on the Robin Hood story was a bit schmaltzy, but was a major Hollywood blockbuster and is still an extremely enjoyable watch. The film has a ton of action, which looked a bit better in the 1990’s, but will still keep you on the edge of your seat.
8. Tin Cup (1996)
This is such an underrated comedy and one of Kevin Costner’s best performances. Cheech Marin is also hilarious in a film that has dozens of memorable one liners. The driving range scene may be the standout though. That crazy Don Johnson…
7. The Big Chill (1983)
Costner has an incredibly brief role. For those who have seen the film, you know exactly what I mean. To those of you who haven’t, no spoilers here. Nonetheless, the film is very good, but sometimes takes itself a bit too seriously…just like the Baby Boomers it portrays.
6. Dances with Wolves (1990)
“Wolves” is nowhere near a bad movie, but it’s just so freaking pretentious and pandering. If you sat down and constructed a Best Picture winner piece by piece, you could do no better than this one. It’s like the sole purpose was to win awards. Again, not bad, but definitely overrated.
5. A Perfect World (1993)
This is a seriously underrated film and shows the nuanced work of Eastwood behind and in front of the camera. Kevin Costner also turns in one of his best performances to date. And that ending…
4. JFK (1991)
Oliver Stone’s conspiracy-filled masterpiece is layered and beautifully-terrifying. The cast is absolutely phenomenal and the story holds up, even after a hefty runtime. Costner is excellent as Jim Garrison. This one has really held up well also…
3. Bull Durham (1988)
Probably the best at capturing the quirkiness that is professional baseball, Bull Durham is a fantastic film with a stellar cast. Costner, Robbins, and Sarandon make Bull Durham consistently hilarious and occasionally poignant. The film has more memorable quotes than all others on this list combined and will change the way you watch a baseball game forever.
2. Field of Dreams (1989)
Field of Dreams is as much about the father-son relationship as it is about baseball. The film plays out like a modern day version of The Odyssey. The prize at the end of Field of Dreams though, is reconciliation and forgiveness. The film has an undeniable weight about it that many other sports movies can only contrive. In my opinion, not only is Field of Dreams the best baseball movie of all-time, but maybe best sports movie as well…
1. The Untouchables (1987)
“The Untouchables” is still a criminally-overlooked movie, that is one of the best films of the 1980’s. Costner is outstanding as moral lawman, Eliot Ness. The supporting cast is also ridiculous, with Andy Garcia, Sean Connery, and of course, Robert De Niro as Al Capone. The story is a familiar one, but unfolds beautifully.