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Best Steven Brill Movies
13th Nov 2025
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Steven Brill, a name synonymous with comedy and family-friendly entertainment, has carved a unique niche in Hollywood. From directing hilarious slapstick to crafting heartwarming stories, Brill's filmography showcases a knack for connecting with audiences of all ages. His films often boast memorable characters, quotable lines, and a comedic timing that has solidified his place as a prominent director. This list celebrates his best work, highlighting the movies that have brought joy and laughter to countless viewers. Now it's your turn! We've compiled a selection of Steven Brill's most popular and critically acclaimed films. Use the drag-and-drop feature to reorder the list below to reflect your personal preferences. Where does your favorite Brill film rank? Share your unique perspective and create your definitive "Best Steven Brill Movies" ranking by simply moving the titles around until they reflect your perfect order!
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#5.
Drillbit Taylor (2008)
5/12
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"Drillbit Taylor" centers on three high school freshmen who, terrified of being bullied, impulsively hire a "bodyguard" named Drillbit Taylor for protection. Unbeknownst to them, Drillbit, played by Owen Wilson, is a penniless con artist and former soldier simply looking for a quick buck and a place to crash. He's woefully unqualified for the job and spends the film devising increasingly ridiculous and ineffective methods of teaching the boys self-defense and navigating high school life, all while trying to hide his true, less-than-heroic nature. The plot thickens as Drillbit's attempts to avoid real work and genuine responsibility lead him into comical and chaotic situations. This film undeniably belongs on a list of "Best Steven Brill Movies" because it perfectly exemplifies his comedic sensibilities and talent for directing. Brill, known for his work on other hilarious comedies like "Heavyweights" and "The Wedding Singer," directs "Drillbit Taylor" with a lighthearted touch, emphasizing the humor in the boys' awkward coming-of-age struggles and Drillbit's own deceptive antics. The film's blend of slapstick, witty dialogue, and heartfelt moments, combined with the chemistry of its cast, showcases Brill's skill in crafting an enjoyable and memorable comedy experience.
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Heavyweights (1995)
#11.0"Heavyweights" (1995) captures the underdog spirit with its story of a group of overweight boys at Camp Hope, a summer haven where self-acceptance and fun are prioritized. This sanctuary is disrupted when the camp is taken over by the ruthless fitness guru Tony Perkis, whose extreme regimen and obsession with weight loss threaten to destroy the boys' summer. The film follows the campers' fight to reclaim their summer, embracing their bodies and forming a strong bond in the face of adversity, a heartwarming tale of friendship, resilience, and ultimately, self-acceptance. This movie earns its place on a "Best Steven Brill Movies" list not only because Brill directed it, but also because of his ability to infuse it with humor and heart. The film beautifully balances slapstick comedy with genuine emotional moments, making it both entertaining and surprisingly touching. Brill's direction highlights the camaraderie amongst the boys and the absurdity of Tony's methods, creating a classic children's movie that resonates with audiences of all ages.
Walk of Shame (2014)
#22.0"Walk of Shame" (2014) follows a driven, ambitious reporter whose carefully crafted life unravels spectacularly after a wild night out. A one-night stand leaves her in a precarious position: stranded in the heart of downtown Los Angeles with no phone, car, identification, or funds. To make matters worse, she has a mere eight hours to navigate the city and make it to the biggest job interview of her career - her dream of becoming a news anchor hangs in the balance. This premise sets the stage for a hilarious and chaotic comedy, showcasing her ingenuity and resilience as she attempts to reclaim control of her life before her career opportunity slips away. While perhaps not a critical darling, "Walk of Shame" is indeed directed by Steven Brill, solidifying its place on a "Best Steven Brill Movies" list. Brill is known for his comedic sensibilities and penchant for creating relatable, slightly exaggerated scenarios. His work often focuses on ordinary people finding themselves in extraordinary situations, and this film perfectly fits that mold. Although the film leans heavily into slapstick and situational humor, Brill's direction effectively guides the pacing and timing, ensuring that the audience is thoroughly entertained by the escalating absurdity of the protagonist's misadventures.
Mr. Deeds (2002)
#33.0Mr. Deeds (2002) perfectly encapsulates Steven Brill's comedic sensibilities. This hilarious remake of the classic film "Mr. Deeds Goes to Town" offers a modern twist on the fish-out-of-water story. When Longfellow Deeds, a small-town pizzeria owner and poet, inherits $40 billion from his deceased uncle, he quickly begins rolling in a different kind of dough. Moving to the big city, Deeds finds himself besieged by opportunists all gunning for their piece of the pie. Babe, a television tabloid reporter, poses as an innocent small-town girl to do an exposé on Deeds, highlighting the satirical nature of fame and fortune that Brill often explores in his work. Brill, known for his directorial work that often balances slapstick humor with heart, provides a lighthearted and entertaining take on this beloved story. The film is packed with memorable gags and a cast of talented comedic actors. While not necessarily a critical darling, "Mr. Deeds" exemplifies Brill's ability to create crowd-pleasing entertainment, a cornerstone of his filmography. The movie’s enduring appeal lies in its clever blend of humor, heartwarming moments, and satirical observations, making it a quintessential entry in the "Best Steven Brill Movies" category.
Without a Paddle (2004)
#44.0"Without a Paddle" sees three childhood friends, adrift in adulthood and experiencing growing distances in their lives, brought together by the death of a fourth. While sorting through their shared past, they find a hidden map detailing a quest their late friend was pursuing – a hunt for the legendary D.B. Cooper's missing loot. Spurred by a sense of adventure and a desire to honor their friend, they embark on this ill-advised journey into the wilderness. Unbeknownst to them, their pursuit of buried treasure is fraught with peril, from untamed rapids to the watchful eyes of dangerous individuals, quickly realizing they're in over their heads. While "Without a Paddle" is not typically considered a masterpiece of filmmaking, it showcases the comedic strengths and directorial style that is consistent throughout Steven Brill's filmography, particularly his talent for blending slapstick, physical comedy, and moments of heartfelt connection, a hallmark of his movies. The film embodies the humorous tone that Brill often brings to his work, the type of film that offers a relatable experience with slapstick humor and an easy-to-follow story, making it a worthy addition to a list of his most well-known and commercially successful work.
Drillbit Taylor (2008)
#55.0"Drillbit Taylor" centers on three high school freshmen who, terrified of being bullied, impulsively hire a "bodyguard" named Drillbit Taylor for protection. Unbeknownst to them, Drillbit, played by Owen Wilson, is a penniless con artist and former soldier simply looking for a quick buck and a place to crash. He's woefully unqualified for the job and spends the film devising increasingly ridiculous and ineffective methods of teaching the boys self-defense and navigating high school life, all while trying to hide his true, less-than-heroic nature. The plot thickens as Drillbit's attempts to avoid real work and genuine responsibility lead him into comical and chaotic situations. This film undeniably belongs on a list of "Best Steven Brill Movies" because it perfectly exemplifies his comedic sensibilities and talent for directing. Brill, known for his work on other hilarious comedies like "Heavyweights" and "The Wedding Singer," directs "Drillbit Taylor" with a lighthearted touch, emphasizing the humor in the boys' awkward coming-of-age struggles and Drillbit's own deceptive antics. The film's blend of slapstick, witty dialogue, and heartfelt moments, combined with the chemistry of its cast, showcases Brill's skill in crafting an enjoyable and memorable comedy experience.
The Do-Over (2016)
#66.0"The Do-Over" (2016) follows Max, a disillusioned bank manager whose mundane life takes a sharp turn when a chance encounter with an old friend, portrayed by Adam Sandler, leads him down a path of deceit and adventure. This friend, a charismatic con artist, convinces Max to fake his own death and embark on a thrilling, albeit dangerous, journey. Suddenly, Max's meticulously planned existence is replaced with high-stakes situations, exotic locales, and a desperate fight to stay alive, all fueled by his friend's elaborate scheme. The premise promises a chaotic blend of comedy and action as Max struggles to navigate this unfamiliar and unpredictable new reality. This film earns its place on a list of "Best Steven Brill Movies" because Steven Brill directed it. Brill is a prolific director known for his collaborations with Adam Sandler, and he has a particular knack for crafting the kind of slapstick, over-the-top comedy that is a hallmark of Sandler's style. Brill also directed "Mr. Deeds," and "Little Nicky," both of which are examples of the films that helped make Sandler a comedic superstar.
Little Nicky (2000)
#77.0"Little Nicky" is a hilarious, albeit critically divisive, comedy that centers around the son of Satan himself. After the devil refuses to hand over the reins of Hell to any of his three sons, the powerful brothers escape to Earth, wreaking havoc and inadvertently closing the portal that funnels sinful souls to the underworld. This weakening blow causes their father, Satan, to rapidly wither away, forcing him to send his youngest and most seemingly inept son, Little Nicky, to Earth to stop his brothers and restore balance to the forces of good and evil. Nicky, with his distinct speech impediment and quirky perspective on the world, must use his limited hellish abilities to save his father and defeat his power-hungry siblings. This zany film rightfully earns its place on a list of the "Best Steven Brill Movies" due to Brill's knack for slapstick humor and his unique directorial vision. While the film features its fair share of potty humor and exaggerated antics, Brill manages to craft a genuinely funny and memorable comedy. "Little Nicky" showcases Brill's ability to blend outrageous scenarios with heart, making it a cult classic and solidifying his spot as a director known for a particular style of comedic storytelling, along with his other works like "Mr. Deeds" and "Heavyweights".
Hubie Halloween (2020)
#88.0"Hubie Halloween" certainly earns its place among the best Steven Brill movies thanks to its masterful blend of slapstick comedy, heartwarming sentimentality, and genuine Halloween spirit. Brill's directorial style, characterized by his ability to create comedic chaos and heartwarming moments within a cohesive narrative, is on full display. The film effectively utilizes the familiar tropes of the holiday, creating a fun and festive atmosphere that will delight audiences of all ages. Furthermore, Brill's direction perfectly allows Adam Sandler to shine, tapping into his strengths to deliver a comedic performance that is both goofy and unexpectedly touching. "Hubie Halloween" proves that Brill excels at crafting films that prioritize humor, heart, and a clear understanding of their target audience. The film successfully provides a feel-good experience, making it a quintessential Steven Brill creation.
Sandy Wexler (2017)
#99.0"Sandy Wexler" offers a heartwarming, albeit slightly uneven, portrayal of the entertainment industry's quirky underbelly. Adam Sandler stars as the titular character, a devoted, if somewhat clueless, talent manager navigating the eccentricities of 1990s Los Angeles. The film, while filled with Sandler's signature humor, delves into themes of loyalty, love, and the pursuit of dreams as Sandy manages a roster of unusual clients. The story pivots when Sandy discovers Courtney Clarke, a gifted singer, setting the stage for a complicated romance against the backdrop of Hollywood's glitz and grime. While "Sandy Wexler" is a relatively low-key Adam Sandler comedy, director Steven Brill's signature touch is evident throughout, solidifying its place in the "Best Steven Brill Movies" list. Brill, known for his ability to extract heartfelt performances and blend comedy with poignant storytelling, crafts a visually engaging narrative. Brill's direction allows for Sandler's comedic talents to shine, while capturing the spirit of the era with a charming, albeit unconventional, love story. His nuanced perspective provides an insight into the world of show business, with a keen eye for portraying both the humor and the vulnerability of its characters, making it a compelling and endearing watch.
Movie 43 (2013)
#1010.0"Movie 43" is a 2013 comedy anthology film structured around a framing device called "The Pitch". In this segment, a deranged screenwriter named Charlie Wessler tries to sell his script to film executive Griffin Schraeder. As Schraeder rejects Wessler's increasingly bizarre ideas, the desperate screenwriter forces him to listen to a series of outlandish short films. These shorts, showcased in the film, are presented as the contents of Wessler's rejected script. While "Movie 43" is often critically panned, its inclusion on a "Best Steven Brill Movies" list is likely a reflection of Brill's involvement as a director. Steven Brill is credited with directing a segment of the film, and his name alone is enough to warrant its inclusion, considering he is the director of other well-known comedies. His contribution, alongside the collective efforts of other directors, contributes to the movie's unique, if controversial, style of comedy.
Too Cool to Be Forgotten
#1111.0"Too Cool to Be Forgotten" is a heartfelt coming-of-age story that perfectly encapsulates the blend of humor, heart, and relatable teenage experiences that define the best of Steven Brill's work. The film showcases Brill's talent for capturing the awkwardness, excitement, and anxieties of youth with a sharp wit and a genuine understanding. His direction provides a nostalgic look back at the 1980s, blending a compelling narrative with memorable characters and a charmingly bittersweet tone, solidifying its place as a standout in his filmography. From the charming performances to the evocative soundtrack, "Too Cool to Be Forgotten" exemplifies the qualities that make Steven Brill a master of the genre. The film’s exploration of themes like first love, self-discovery, and the bittersweet passage of time resonate deeply with audiences, showcasing Brill's ability to craft narratives that are both entertaining and emotionally resonant. It’s a quintessential example of Brill's directorial style, offering a nostalgic journey that celebrates the joys and pains of adolescence, cementing its place as a must-watch for any fan of his work.
7:30 Drinks
#1212.0"7:30 Drinks" is a quintessential Steven Brill film, showcasing his talent for crafting witty and character-driven comedies. This short film, much like Brill's feature-length successes, excels at capturing the awkwardness and humor found in everyday human interactions. The film's focus on a simple, relatable scenario – a casual meeting for drinks – allows Brill to mine comedic gold through sharp dialogue and perfectly timed physical comedy. The film's strength lies in its ability to build tension and anticipation, culminating in a satisfyingly absurd payoff, a signature element of Brill's comedic style. Furthermore, "7:30 Drinks" highlights Brill's keen eye for casting and direction. The actors, guided by Brill's clear vision, deliver performances that are both hilarious and believable. The film's concise storytelling demonstrates Brill's mastery of pacing and his ability to effectively utilize the limited timeframe to establish compelling characters and a memorable narrative arc. "7:30 Drinks" perfectly encapsulates the essence of Brill's comedic sensibility, making it a deserving addition to any list celebrating the "Best Steven Brill Movies."
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