Every 30 for 30 Baseball Doc, Ranked

Baseball has often felt like it gets short shrift from ESPN's venerable film production unit, but tonight's debut of The Captain could change that. The new seven-part docuseries is a clear attempt to build on the success of the channel's phenomenal Michael Jordan series The Last Dance with another sports figure who's existed in the firmament of his sport since long before he retired, Derek Jeter.

Whether Jeter proves to be even a fraction of the fascinatingly complex personality that Jordan was remains to be seen (it's a tall order, and Yankee-haters will certainly have their knives out), but regardless of the outcome, The Captain gives us a chance to reflect on ESPN's previous baseball documentaries under the banner of the 30 for 30 series. Each of these films can be streamed on ESPN's subscription streaming platform, ESPN+.

14. Four Days in October

Season 1, Episode 24
Air date: October 5, 2010

It came as no surprise that the 30 for 30 enterprise — the brainchild of former ESPN personality, founder of The Ringer, and mascot for Boston sports fans everywhere — would eventually turn its gaze to the 2004 Boston Red Sox, who broke their nearly century-long drought and finally bested the New York Yankees en route to winning the World Series. 30 for 30 is almost always better when the subjects haven't been already covered to death, and sure enough Four Days in October adds precious little to this oft-told tale.

13. The House of Steinbrenner

Season 1, Episode 22
Air date: September 21, 2010

Oscar-winning director Barbara Koppel brought a hefty pedigree to this doc about the longtime Yankee owner that centers itself around the demolition of the old Yankee Stadium and the opening of the new one. Unfortunately, the doc never seems to settle in to the most interesting aspects of its story, namely Steinbrenner's reign of terror in the '70s and '80s, and too often relies on pat Yankee reverence.

12. Little Big Men

Season 1, Episode 19
Air date: August 31, 2010

This story about the 1982 Little League World Series champions, an American team that upset the heavily favored Taiwanese squad, had all the makings of a powerful story about the expectations we put on kids in athletics. Unfortunately director Al Szymanski drowns the film in hushed, flowery voiceover that is ultimately far more distracting than it is mood-setting.

11. Long Gone Summer

Season 4, Episode 6
Air date: June 14, 2020

The 1998 home run chase between Mark McGwire and Sammy Sosa is another story that been told so many times, and director AJ Schnack's film doesn't have anything too terribly insightful to add about baseball's relationship with performance-enhancing drugs.

10. Deion's Double Play

Season 2, Episode 27
Air date: January 31, 2019

This story, about Atlanta Braves star Deion Sanders and his attempts to carry off a career as a two-sport athlete — in particular trying to play in both an NFL football game and a Major League Baseball playoff game on the same day — benefits greatly from Sanders's outsized personality serving as both narrator and carnival barker.

9. Jordan Rides the Bus

Season 1, Episode 18
Air date: August 24, 2010

It was the biggest story in sports when Michael Jordan quit the NBA to play minor league baseball for the White Sox franchise. The problem, with both Jordan Rides the Bus and more recently with The Last Dance, is that it still feels like we've ever gotten the full story about this from Jordan (or anyone else in the know). Still, director Ron Shelton (Bull Durham) knows baseball and brings a lot of intelligence and fascination to this flick.

8. You Don't Know Bo

Season 2, Episode 6
Air date: December 8, 2011

The story of Bo Jackson, the athletic phenom who played both football and baseball at a world-class level, is a story worth telling, especially because Jackson's importance as a pro athlete seems to have been largely wiped from public memory. Director Michael Bonfiglio harnesses Jackson as a compelling subject and guides the viewer through his career-ending injury that's more heartbreaking than you probably remember.

7. Brothers in Exile

Season 2, Episode 24
Air date: November 4, 2014

Cuban pitchers Livan and Orlando Hernandez both defected to the United States to play professional baseball, but their stories transcend sports. For an MLB Productions documentary, there's a lot of meat on the bone of this story, from ultra-rare footage of the brothers pitching in Cuba to the stories of how they made it out of Castro's regime, and what that cost them.

6. The Day the Series Stopped

Season 2, Episode 21
Air date: July 14, 2016

The 1989 Loma Prieta earthquake looms large in the memories of sports fans because it was experienced live on television as ABC was beginning its broadcast of a World Series game between the San Francisco Giants and Oakland Athletics. Director Ryan Fleck packs his film with interviews, recollections, and news footage. The baseball of it all remains something of a tenuous connection to an undoubtedly riveting true-life tale.

5. Doc & Darryl

Season 3, Episode 10
Air date: July 14, 2016

New York Mets superstars Dwight "Doc" Gooden and Darryl Strawberry were part of the legendary 1986 World Series championship team that captivated New York City. The arcs of their careers, both falling short of greatness due to substance abuse issues, will tie them forever to each other in the public's mind. Watching them both look back on careers that reached insane heights but still fell short of expectations is a psychologically complex and emotionally sensitive task for directors Judd Apatow and Michael Bonfiglio.

4. Fernando Nation

Season 1, Episode 27
Air date: October 26, 2010

The career of phenomenally popular Los Angeles Dodgers pitcher Fernando Valenzuela, who at age 20 emigrated from Mexico would already make for a perfect 30 for 30 subject. But director Cruz Angeles intertwines Valenzuela's story with the story of the Dodgers' spotty history with the Mexican population of Los Angeles, which was displaced to make room for Dodger Stadium and which only started to come around to the team with Valenzuela's ascent.

3. Silly Little Game

Season 1, Episode 11
Air date: April 20, 2010

You'd think the story of the invention of "rotisserie league baseball" — what would grow into the empire we now know as fantasy sports — wouldn't be a thrilling enough topic for a sports documentary. But this doc is the definition of digging out a story that nobody knew about and telling it with all of its strange characters and small-scale dramas. It's improbably fascinating.

2. Once Upon a Time in Queens

Season 4, Episode 11
Air date: September 14, 2021

Back with the '86 Mets again, the rare team whose story has been told a hundred times and still manages to retain its interest. Ranking a four-part 30 for 30 doc might seem like cheating — and initially it seems like a hefty ask for a doc about just one team — but this really was a cast of characters that hit New York at a fascinating turning point for the city. Letting the story stretch its legs and breathe while folks like Keith Hernandez, Darryl Strawberry, and Lenny Dykstra recount what led up to the 1986 World Series is time well spent.

1. Catching Hell

Air date: September 27, 2011

Catching Hell is 30 for 30 at its best, digging into a story that was all headlines — in this case the Chicago Cubs fan who inadvertently interfered with a foul ball, setting off a chain reaction that led the beleaguered team to lose the National League Championship Series in 2003 — and getting to the human story at its heart. The heartbreaking story of the abuse rained upon Steve Bartman by his fellow Cubs fans is a cautionary and shameful lesson for sports fans everywhere, and ace documentary filmmaker Alex Gibney breaks down the moment as if he's forming an airtight case that this kind of thing could have happened to any one of us.

The Captain premieres on ESPN and ESPN+ Monday July 18, after the MLB All Star Home Run Derby

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Joe Reid is the senior writer at Primetimer and co-host of the This Had Oscar Buzz podcast. His work has appeared in Decider, NPR, HuffPost, The Atlantic, Slate, Polygon, Vanity Fair, Vulture, The A.V. Club and more.