Every Anna Boden & Ryan Fleck Movie, Ranked Worst To Best

Since 2006, Anna Boden and Ryan Fleck have written and directed several movies together, which have had varying degrees of success, but are all worth checking out, including their newest film, Freaky Tales. Boden and Fleck first met at NYU in the early 2000s during a filmmaking course, where the two bonded over their shared love of movies. Soon after, they directed a short film together called Gowanus, Brooklyn, which won the Grand Jury prize at the 2004 Sundance Film Festival. It wasn’t long before the directors were tackling their first feature film, and the many more that came after.

Altogether, Boden and Fleck have written and directed six movies together. At times, the two have taken on separate roles in the filmmaking process, with Fleck acting as director and Boden acting as editor, yet for the most part, the directing process has been split evenly between the two. Generally, this has worked out well for the pair, as most of their films have garnered critical success. Even then, when going through their movies with a fine-tooth comb, you can see which come out on top, and which are more forgettable.

6

It’s Kind Of A Funny Story

A Teenager Checks Himself Into A Mental Health Facility

When ranking Boden and Fleck’s movies from worst to best, it is inevitable that we start with 2010’s It’s Kind of a Funny Story. Based on a young adult book of the same name by Ned Vizzini, it tells the story of Craig, a teenage boy who decides to check himself into a mental health facility after facing overwhelming anxiety and suicidal ideation. Upon finding that the youth wing is closed, Craig must spend his time with the adults in the clinic, who inspire him in unexpected ways.

Though It’s Kind of a Funny Story has a well-intentioned story, it doesn’t fully deliver. With a 59% on Rotten Tomatoes, critics noted that the film’s optimistic story, set within a psych ward, may not be the best representation of mental health issues. Furthermore, some felt that the movie tried too hard to be earnest without really diving deep into its themes. Fortunately, one bright spot is the performances by Zach Galifianakis, Keir Gilchrist, and Emma Roberts.

5

Mississippi Grind

A Man Brings His Good Luck Charm To The Casino

The next Boden and Fleck movie that left some viewers disappointed was Mississippi Grind. In this film, a struggling gambler named Gerry meets a younger, luckier gambler named Curtis. After a night of drunken fun, Gerry finds himself being hunted by a loan shark. Desperate for more cash, he enlists Curtis to go on a gambling trip with him. This leads to some dangerous bets and revelations about what the men truly want out of their lives.

From the critics’ perspective, Mississippi Grind is a great movie, worthy of a Certified Fresh 91%. These reviewers were impressed with the film’s ability to balance humor and darkness, and enjoyed the chemistry between the lead actors, Ben Mendelsohn and Ryan Reynolds. On the other hand, audiences were less thrilled by the film, giving it a middling 55%. Viewers felt that the movie was often boring, and the story went to places they weren’t expecting.

4

Freaky Tales

Four People’s Lives Intertwine In Oakland, California

Firmly in the middle of Boden and Fleck’s best and worst movies is their latest endeavor, Freaky Tales. Released at the beginning of April 2025, this movie follows four different characters whose lives intertwine in Oakland, California in 1989. The movie stars Pedro Pascal, Jay Ellis, Normani, Dominique Thorne, and Ben Mendelsohn. Freaky Tales is based on Fleck’s own experiences growing up in Oakland in the 1980s, and is a love letter to the city and its culture.

Freaky Tales isn’t a perfect movie, but it is one that is easy to enjoy. With a 71% critics score and an 87% audience score on Rotten Tomatoes, audiences were entranced by the movie’s colorful, brash atmosphere and the strong performances by its cast. It is clear that Fleck and Boden were both completely invested in this story. However, one drawback to Freaky Tales is that it is more vibes than substance. Those seeking a deep, detailed tale may want to look elsewhere.

3

Captain Marvel

An Alien Warrior Tries To Uncover Her Past

One of Boden and Fleck’s most controversial yet impactful movies by far is Captain Marvel. This 2019 superhero movie follows Captain Marvel, a Kree warrior living in 1995 America who is plagued with visions of a past life, where she was an Air Force pilot named Carol Danvers. With help from Nick Fury, she tries to figure out where she came from and who she really is. Notably, Boden and Fleck did not go on to direct the sequel, The Marvels.

Before, during, and after Captain Marvel’s release, the movie was plagued with poor reviews, now known as review bombing. For the most part, this had to do with the movie’s feminist themes and Brie Larson’s own activism. Based on critics’ scores, Captain Marvel actually comes in at a strong Certified Fresh 79%. Despite some clichés and a lack of big, impressive moments, the movie received praise for its wonderful performances and nostalgic story. It says something that Captain Marvel has continued to play a role in the MCU since her introduction.

2

Sugar

A Dominican Man Dreams Of Playing Professional Baseball

In the second place spot for Boden and Fleck’s best movie is Sugar. It revolves around a young man named Miguel “Sugar” Santos who dreams of leaving the Dominican Republic for a chance to play for an American professional baseball team. Using his talents for pitching, his dream comes true, and he lands a spot playing in Iowa. Yet, faced with intense culture shock and racist ideals, Sugar’s experience is not as incredible as he might have hoped.

Sugar is the first movie that Boden and Fleck directed together, and it is definitely an underrated classic. Not only does the movie tell an important story about race and prejudice in America, but it also does so in a way that avoids many of the clichés present in other sports dramas. Boden and Fleck handle Sugar’s story with care and realism, making it an even more important watch. All in all, Sugar is a movie that viewers should be putting on their to-watch list.

1

Half Nelson

A Middle School Teacher Forms A Bond With His Student

Finally, what has to be Boden and Fleck’s best movie so far is their first: Half Nelson. Written by the pair and directed by Fleck, Half Nelson follows a middle school teacher who spends his days teaching history and his nights getting high. After being caught in a drug-induced haze by a young student whose brother is in jail for drug dealing, the teacher forms a bond with her and tries to step up as a better role model. The cast includes Ryan Gosling and Anthony Mackie.

Half Nelson boasts Boden and Fleck’s best Rotten Tomatoes scores yet with a Certified Fresh 91% critics score and an 82% audience score. The movie is dark, humorous, and unflinching in its portrayal of its lead character, and takes on countless issues such as drugs, race, and class. Overall, Half Nelson is Boden and Fleck’s best attempt at telling a story that toes the line between blatant sadness and hope. After catching Freaky Tales in theaters, viewers must check out Half Nelson.