All-Time Classic Baseball Movies You Need to Watch

“Fear Strikes Out” (1957)

This moving and inspirational movie is based on former Boston Red Sox star Jimmy Piersall, who detailed his struggles with Bipolar disorder in his book, Fear Strikes Out: The Jim Piersall Story.

Anthony Perkins betrays Jimmy Piersall, who struggles with the pressure of playing well at the professional level while also wanting to make his father proud.

One of the first true iconic baseball films, Fear Strikes Out also put the late Robert Mulligan on the map as a five-star movie director. This was his first big film, and he went on to direct other blockbusters such as To Kill a Mockingbird (1962) and The Man in the Moon (1991).

This is a must-see film for any major fan of the Red Sox, who’ve been featured in other blockbuster films like Fever Pitch (2005) and Good Will Hunting (1997). Speaking of the Red Sox, fans will soon be able to place wagers on their favorite MLB team through apps such as Caesars sportsbook Massachusetts. 

The hope is that Massachusetts will launch legalized sports betting at some point in 2023, and Caesars Massachusetts will likely offer new users a risk-free wager once the sportsbook launches.

“A League of Their Own” (1992)

This star-studded film includes Tom Hanks (Jimmy Dugan), Madonna (Mae Mordabito), Geena Davis (Dottie Hinson), Rosie O’Donnell (Dorris Murphy), Anne Ramsay (Helen Haley) and Lori Petty (Kit Keller).

A League of Their Own focuses on the All-American Girls Professional Baseball League, which was formed in World War II. Many of the top players of Major League Baseball left to fight in the war. So an all-women’s baseball league was formed with the idea of maintaining strong public interest in America’s pastime.

This 1992 film tells a fictionalized story of the All-American Girls Professional Baseball League. Dottie emerges as the team leader of the Rockford Peaches (managed by Hanks’ character, Dugan).

While Dottie and the Peaches aim for championship glory, several players must learn to overcome personal hardships. For instance, Dottie has a falling out with her sister, Kit, who joins a rival team in the Racine Belles.

A League of Their Own remains one of the top must-see baseball movies more than 30 years after its release. This should be at or near the top of your sports movies watch list.

“The Sandlot” (1993)

David Mickey Evans directed this timeless blockbuster that has entertained generations for three decades (and counting).

The Sandlot tells the story of a boy named Scott Smalls (played by Tom Guiry) who moves to a Los Angeles suburb with his family in the summer of 1962. Smalls befriends a bunch of boys who play baseball at a nearby diamond (“The Sandlot”). Baseball thus becomes Smalls’ favorite summer hobby, and he becomes closer with the friends over time.

But Smalls gets into trouble when he lets his friends play with a baseball owned by his stepfather. The problem? The ball was owned by none other than MLB icon ‘Babe’ Ruth, and to make matters worse, the ball was hit over the sandlot fence and into the backyard of a neighbor who owns an aggressive dog.

So, Scott and his friends must come up with a plan to get the baseball back a) before the stepfather finds out and b) without being harmed by the angry and opportunistic dog..

The cast of The Sandlot also includes Mike Vitar (Benny “The Jet” Rodriguez) and Brandon Quintin Adams (Kenny DeNunez). 

Fans of ‘90s sports movies may recognize Vitar and Adams as actors in The Mighty Ducks film series. Vitar played Luis Mendoza in the second and third installments, and Adams played Jesse Hall in the first two.

“Moneyball” (2011)

This 2011 blockbuster stars Brad Pitt as Billy Beane, the real-life longtime Oakland Athletics’ executive vice president of baseball operations.

Beane has become a legend in the baseball world for his ability to build elite teams with low payrolls and limited financial resources. The film is based off of Michael Lewis’ 2003 book, Moneyball: The Art of Winning an Unfair Game.

Unlike many big market teams, Beane and the Athletics didn’t use giant sums of dollars to pay top players. Instead, they focused on advanced stats, analytics, sabermetrics and unique sciences to evaluate and develop top-level players.

This film focuses on the 2002 Athletics, who won 103 games and the AL West division despite losing three superstars in Jason Giambi, Johnny Damon and Jason Isringhausen in free agency.

Pitt received an Academy award for Best Actor nomination for his role as Beane (Colin Firth won it for his role as King George VI in The King’s Speech). The film grossed $110.2 million at the box office.