10 Boarding School Movies To Watch After The Holdovers

Alexander Payne’s The Holdovers follows a teacher looking after students with nowhere to go over Christmas break and is one of many movies that explores the trials and tribulations of boarding school life. Focusing primarily on the curmudgeonly history teacher Paul Hunham, played by Paul Giamatti, and the troubled unruly student Angus Tully, played by Dominic Sessa in his feature debut, the film has a 1970s look, aesthetic, and setting. The Holdovers is also comparable to classic Christmas movies such as It’s a Wonderful Life and Hal Ashby films like Harold and Maude and The Last Detail.

The boarding school setting of The Holdovers brings to mind a whole host of other movies with a similar setting. The situation of young students discovering themselves far away from home has produced many incredible films focusing on dissatisfied pupils, rebellious outliers, and even magical orphans. While it looks set to become a classic holiday film, just as importantly, The Holdovers joins a long lineage of boarding school movies exploring identity, growing up, and friendship.

10

Dead Poets Society (1989)

Robin Williams Plays A Teacher Who Wants His Students To Make The Most Out Of Life.

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Dead Poets Society

PG

Drama

Documentary

9.8/10

Release Date

June 2, 1989

Runtime

128 minutes

Director

Peter Weir

Writers

Tom Schulman

Cast

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  • Headshot Of Robin Williams In The 2006 AmFAR Cinema

    Robin Williams

  • Headshot Of Robert Sean Leonard

    Robert Sean Leonard

Set in an all-boys prep school in the 1950s, Dead Poets Society follows John Keating (Robin Williams), an English who inspires his students to appreciate poetry, think critically, and see life from a new perspective. The cast also includes Ethan Hawke, Robert Sean Leonard, and Josh Charles.

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There are a lot of comparisons to be made between The Holdovers and Dead Poets Society. Both films include groups of lost young men in preparatory boarding schools searching for meaning and an older teacher figure devoted to seeing them excel. Robin Williams’s performance as the inspirational teacher John Keating, who encourages his students to “seize the day,” is in stark contrast to Paul Giamatti’s strict classics teacher in The Holdovers, Paul Hunham. The films can be seen as two sides of the same coin and as heartfelt explorations of how the bonds shared with authority figures can help influence a person’s development growing up.

At its core, Dead Poets Society is about youthful rebellion and the search for meaning within the confines of tradition. Like The Holdovers, Dead Poets Society examines the nuanced relationships between teachers and students, highlighting the power of mentorship and intellectual curiosity. The film’s themes of self-discovery, nonconformity, and the weight of societal expectations make it a compelling watch for those drawn to narratives about individuals who challenge authority and forge their own paths. Also like The Holdovers, its emotional depth and poignant ending leave a lasting impression.

Collage of Mary Shelley looking up in Mary Shelley, John Keating smiling in Dead Poets Society, and John Nash looking concerned in A Beautiful Mind

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9

If…. (1968)

Lindsay Anderson’s Film Is About An Unruly Schoolboy Dissatisfied With The Way Things Are Done

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If….

R

Drama

Crime

Release Date

May 21, 1969

Runtime

111 Minutes

Director

Lindsay, Anderson

Writers

David Sherwin, John Howlett

Cast

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  • Headshot Of Malcolm McDowell

    Malcolm McDowell

  • Cast Placeholder Image

    David Wood

  • Cast Placeholder Image

    Richard Warwick

  • Cast Placeholder Image

    Christine Noonan

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Lindsay Anderson’s 1968 satirical drama If…. features the late ’60s and early ’70s aesthetic that The Holdovers director Alexander Payne attempts to recreate in his movie. If…. was the subject of controversy when it was released for its depictions of violence, but it’s a landmark film of British countercultural cinema. In If…., the anti-establishment attitude and dissatisfaction felt by Malcolm McDowell’s rebellious student character, Mick Travis, is similar to Dominic Sessa’s excellent portrayal of Angus Tully in The Holdovers.

Fans of The Holdovers will appreciate its layered depiction of student dissatisfaction and the growing resentment toward an institution that seeks to suppress individuality.

If’s political undertones and commentary on class structure give it a depth that extends beyond a typical coming-of-age story. Fans of The Holdovers will appreciate its layered depiction of student dissatisfaction and the growing resentment toward an institution that seeks to suppress individuality. The stark contrast between the school’s authoritarian rule and the students’ yearning for freedom makes for a gripping watch. Like The Holdovers, If…. presents an intimate look at the personal and societal factors that drive individuals toward rebellion.

8

Wild Child (2008)

Emma Roberts Stars In A Journey Of Finding Meaning Through Friendship

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Wild Child

PG-13

Comedy

Release Date

August 15, 2008

Runtime

98 Minutes

Director

Nick Moore

Writers

Lucy Dahl

Cast

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The 2008 teen comedy Wild Child, starring Emma Roberts, appears to have little in common with the deep probing examination of loneliness and personal tragedy that is The Holdovers on the surface. However, upon further examination, both films, at their core, are about finding meaning in life through unlikely friendships. Like many of the boarders in Alexander Payne’s film, Wild Child‘s Poppy Moore, played by Roberts, is a wealthy, rebellious, spoiled student who has been sent to boarding school to learn the meaning of discipline and respect, and who eventually discovers the value in such institutions.

Wild Child also explores themes of belonging and the importance of genuine connections, much like The Holdovers. Poppy’s initial culture shock and defiance gradually give way to an appreciation for her new home, much like how Paul Hunham in The Holdovers undergoes his own transformation. Despite being significantly more lighthearted than The Holdovers, Wild Child still captures the universal struggle of adapting to change and finding one’s place in the world, making it a fitting choice for fans of character-driven boarding school dramas.

7

The Riot Club (2015)

A Movie Showing The Darker Side Of Private Education

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The Riot Club

R

Drama

Thriller

Release Date

March 27, 2015

Runtime

107 Minutes

Director

Lone Scherfig

Writers

Laura Wade

Producers

Graham Broadbent, Peter Czernin, Peter Watson, Steve Norris, Tessa Ross, Lizzie Francke, Sam Lavender, Thorsten Schumacher

Cast

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  • Headshot Of Sam Claflin

    Sam Claflin

    Miles Richards

  • Headshot Of Max Irons

    Max Irons

    Alistair Ryle

  • Headshot Of Douglas Booth

    Douglas Booth

    Harry Villiers

  • Headshot Of Jessica Brown Findlay

    Jessica Brown Findlay

    Lauren

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2015’s The Riot Club showcases the darker side of the exclusionary and conceited nature of private education. Featuring the same type of promising young men who attend the Barton Academy in The Holdovers, The Riot Club is inspired by the real-life Bullingdon Club for Oxford University students in Britain. The entitled members of this elite club have no issue acting out violence on those they perceive as lower than them and are exactly the type of hedonistic, arrogant, and pompous students that teacher Paul Hunham despises in The Holdovers.

This mirrors The Holdovers’ focus on flawed, multi-dimensional characters navigating the pressures of their environment.

Beyond its critique of upper-class excess, The Riot Club also presents a compelling psychological study of its characters, exploring how ambition and peer pressure drive them toward destructive choices. This mirrors The Holdovers’ focus on flawed, multi-dimensional characters navigating the pressures of their environment. The Riot Club’s exploration of privilege, morality, and the cost of belonging provides a thought-provoking companion piece to the themes of personal accountability found in The Holdovers.

6

The History Boys (2006)

The Adaptation Sees Students Hoping To Secure Places At Elite Colleges

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The History Boys

R

Comedy

Documentary

Drama

Release Date

October 2, 2006

Runtime

104 minutes

Director

Nicholas Hytner

Cast

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    Samuel Anderson

  • Headshot Of James Corden

    James Corden

  • Headshot Of Stephen Campbell Moore

    Stephen Campbell Moore

  • Headshot Of Richard Griffiths In The Premiere Of Harry Potter

    Richard Griffiths

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Based on a play by Alan Bennett, The History Boys is about a group of British teenagers encouraged by their teachers to secure places in the elite colleges Oxford and Cambridge. Spearheaded by the beloved General Studies teacher, Hector (Richard Griffiths), a kind and affectionate educator, he is the opposite of the teacher Paul Hunham in The Holdovers, but at their core, the two just want to see young men succeed. The History Boys features a young James Corden among its ensemble cast and is a funny, heartfelt, and intimate movie.

The History Boys, much like The Holdovers, also explores the dynamics between students and teachers, the purpose of education, and the conflicts between different teaching philosophies. Hector’s unorthodox teaching style challenges the rigid academic expectations placed on his students, much like Paul Hunham’s approach to his small group of stranded students in The Holdovers. Fans of The Holdovers will also appreciate The History Boys’ focus on the bonds formed within an academic setting, as well as the way both films highlight the tensions between tradition and progressive thinking.

5

She’s The Man (2006)

Amanda Bynes And Channing Tatum Star In A Modern Retelling Of A Classic Shakespeare Comedy

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She’s the Man

PG-13

Comedy

Romance

Sports

8/10

Release Date

March 17, 2006

Runtime

105 Minutes

Director

Andy Fickman

Writers

Ewan Leslie, Karen McCullah Lutz, Kirsten Smith

Cast

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  • Headshot Of Amanda Bynes

    Amanda Bynes

  • Headshot Of Channing Tatum

    Channing Tatum

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An outrageous modern retelling of a classic play, the romantic comedy She’s the Man is loosely based on William Shakespeare’s Twelfth Night. Like The Holdovers, this film takes place at an elite boarding school, with Amanda Bynes starring as a teen girl pretending to be her older brother. While the lighthearted She’s the Man, which is one of the most underrated coming-of-age comedies, takes a much sillier turn than the intense drama that can be found in Alexander Payne’s film, there are several surprising paralells.

Like The Holdovers, She’s The Man focuses on characters who find themselves through adversity and personal conflict within an institutional setting. The film blends its easygoing humor with deeper reflections on self-perception and belonging, exploring similar territory as the more poignant moments of The Holdovers – where characters are forced to confront their vulnerabilities and discover their true selves amid the rigid structure of boarding school life – but through a much less serious lens.

4

St Trinian’s (2007)

The British Comedy That Celebrates The Rebellion Of School Days

A large group of schoolgirls in uniform with Talulah Riley's Annabelle in front in St Trinian's.

Much like She’s The Man and Wild Child, 2007’s St Trinian’s has more in common with The Holdovers than it first seems on the surface. The dysfunctional students of St. Trinian’s boarding school for girls are reminiscent of the disorder and dissatisfaction of the boys from Barton Academy in The Holdovers. However, the experience of the shy transfer student Annabelle Fritton (Talulah Riley) in St. Trinian’s is much different than that of Barton Academy international student Ye-Joon Park from Korea, who is seen crying and wetting the bed as he misses his family. Instead, after overcoming initial harassment, Annabelle embraces the school’s rebellious side and becomes an important part of the plan to save the school from financial ruin.

St. Trinian’s portrays a group of girls who band together to save their school, exhibiting the same sense of unity and rebellion that The Holdovers’ characters display as they confront their own personal struggles.

In both films, the boarding school setting serves as a backdrop for developing relationships and finding empowerment through unlikely alliances. St. Trinian’s portrays a group of girls who band together to save their school, exhibiting the same sense of unity and rebellion that The Holdovers’ characters display as they confront their own personal struggles. The unconventional, offbeat tone of St. Trinian’s will resonate with viewers who appreciate the more humorous side of institutional life and the quirky characters who thrive in such environments.

3

The Chorus (2004)

The Oscar-nominated French Drama Follows A Teacher Who Wants To Make A Positive Impact

Gérard Jugnot as Clément Mathieu conducting students in the 2004 movie The Chorus (Les Choristes)

The opening scene of The Holdovers features the singing choir of Barton Academy, in a song that introduces the audience to the world of the film, before focusing on other characters. The French musical drama The Chorus focuses entirely on a boarding school choir, inspired by the real-life Little Singers of Paris. This movie features a new teacher who is inspired to positively affect his student’s lives through the power of music. Much like The Holdovers, it is a moving examination of the way a decent teacher can transform his students from unruly boys into productive young men.

The focus on music as a source of hope and discipline in The Chorus mirrors the subtle emotional undercurrents of The Holdovers, where characters, especially the young students, find their own forms of self-expression and healing amid their struggles. The bonds formed between the teacher and students in The Chorus evoke similar themes of mentorship and the sometimes surprising ways in which people open up to one another when placed in a shared, structured environment. Both films resonate with audiences who enjoy emotional stories where individuals find redemption and a sense of belonging within the confines of a boarding school.

2

All I Wanna Do (1998)

The Early Kirsten Dunst Comedy Sees The Merging Of Male And Female Students

Rachel Leigh Cook's Abby and Kirsten Dunst's Verena stand in an office in school uniforms in All I Wanna Do

Troubled student Angus Tully sorely feels the lack of female students at Barton Academy in The Holdovers. However, in the comedy All I Wanna Do the opposite is true, as it features an all-girls preparatory school that is planning to merge with a nearby all-boys academy. This film’s coming-of-age themes of growing up, lust, and rebellion, are similar to the journey of self-discovery and friendship seen in The Holdovers. This film is set against a backdrop of the ’60s, and much like the Alexander Payne film, harks back to an earlier time for culture and society.

Much like the humor and camaraderie found in The Holdovers, All I Wanna Do celebrates the strong bonds formed during times of shared struggle against authority. The girls’ collective effort to save their school from outside forces reflects the relationships formed among the characters in The Holdovers who, despite differing backgrounds, come together in unexpected ways. Both films feature a deep sense of identity and community, where personal development is sparked by resistance to change, making All I Wanna Do an enjoyable choice for fans of The Holdovers who appreciate the blend of humor, rebellion, and emotional growth within a boarding school context.

A collage of Kirsten Dunst in Bring It On, Interview With A Vampire, and The Power of the Dog

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1

Harry Potter And The Sorcerer’s Stone (2001)

The First Harry Potter Movie Finds Meaningful Connections In A Boarding School

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Harry Potter and the Sorcerer’s Stone

PG

Adventure

Family

Fantasy

38

8.4/10

Release Date

November 16, 2001

Runtime

152 Minutes

Director

Chris Columbus

Writers

J.K. Rowling, Steve Kloves

Sequel(s)

Harry Potter and the Chamber of Secrets, Harry Potter and the Prisoner of Azkaban, Harry Potter and the Goblet of Fire, Harry Potter and the Order of the Phoenix, Harry Potter and the Half-Blood Prince, Harry Potter and the Deathly Hallows – Part 1, Harry Potter and the Deathly Hallows: Part 2

Cast

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  •  Headshot of Daniel Radcliffe In The London screening of 'The Lost City'

    Daniel Radcliffe

  • Headshot Of Rupert Grint

    Rupert Grint

The beginning of the adaptations of one of the most-read fantasy novel series, Harry Potter and the Sorcerer’s Stone, was directed by Chris Columbus and follows the titular Harry Potter as he discovers he has magical powers. Living with his cruel aunt and uncle, the orphaned Harry lives a challenging life that is changed when he meets a gentle giant named Hagrid, who spirits him away to Hogwarts School of Witchcraft and Wizardry, where he soon learns his destiny.

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When you take away all the magic, witchcraft, and wizardry, the boarding school drama of Harry Potter and the Sorcerer’s Stone is not all that dissimilar to The Holdovers. Orphaned wizard Harry’s sense of abandonment and difficult family circumstances, mimics the boarding student Angus Tully’s lonely Christmas stuck at Barton Academy. The difference is that while Harry finds escapism and meaning through the people he meets at the wondrous magical school of Hogwarts, Angus finds his educational institution restricting and dull. However, the two characters both face challenges and take solace in the mentor figures they meet — Dumbledore for Harry, and Paul Hunham for Angus.

The connections made between characters in Harry Potter are central to the story’s emotional depth, much like the evolving bonds in The Holdovers.

The connections made between characters in Harry Potter are central to the story’s emotional depth, much like the evolving bonds in The Holdovers. Harry’s struggles with isolation, finding friends who become a surrogate family, align with the themes of emotional discovery and the importance of mentorship that The Holdovers explores. Fans of The Holdovers will be drawn to Harry Potter’s exploration of youth, identity, and the dynamics between students and mentors, as both films offer poignant takes on how personal growth and finding a sense of home can occur within the walls of a boarding school, albeit one filled with magic or not.

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The Holdovers

R

Comedy

Drama

Holiday

ScreenRant logo

7/10

Release Date

November 10, 2023

Runtime

133 Minutes

Director

Alexander Payne

Writers

David Hemingson

Cast

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  • Headshot Of Paul Giamatti

    Paul Giamatti

  • Cast Placeholder Image

    Da’Vine Joy Randolph

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