8 Movies Like The Holdovers That Deserve Your Attention

Directed by Alexander Payne, ‘The Holdovers‘ is a comedic drama that centers around the character of Paul Hunham (Paul Giamatti), who is universally disliked by students and faculty alike due to his pomposity and rigid demeanor. Stranded at the school over the Christmas holiday in 1970 with no family and no escape plan, Paul finds himself overseeing a handful of students unable to journey home. The primary focus becomes Angus (Dominic Sessa), a troublesome 15-year-old with a penchant for misbehavior, and Mary (Da’Vine Joy Randolph), the head cook coping with the recent loss of her son in Vietnam.

Together, this unlikely trio, stranded in a snowy New England landscape, forms an unexpected Christmas family, navigating through humorous misadventures and discovering that, despite their disparate backgrounds, they can shape their own futures beyond the constraints of their pasts. The film delves into the dynamics between Paul, Angus, and Mary, emphasizing their shared journey of self-discovery and mutual understanding.

As the narrative unfolds during the two snowy weeks in New England, ‘The Holdovers’ beautifully illustrates how these three individuals, seemingly shipwrecked in their own lives, come together to forge a new sense of belonging and purpose. The stellar cast, led by Paul Giamatti and Da’Vine Joy Randolph, brings depth to this heartwarming tale of resilience, friendship, and the transformative power of shared experiences. Here are more movies like ‘The Holdovers’ that string the same heart-warming chords.

8. The Squid and the Whale (2005)

‘The Squid and the Whale,’ directed by Noah Baumbach, is a poignant exploration of a family in the midst of divorce, capturing the emotional complexities with a mix of humor and drama. Similarly, ‘The Holdovers,’ helmed by Alexander Payne, depicts unlikely connections and personal growth within an unconventional Christmas family. Both films delve into the intricacies of relationships and showcase characters navigating through challenging circumstances. While ‘The Squid and the Whale’ focuses on a fractured family, ‘The Holdovers’ unfolds the transformative power of unexpected bonds, making them complementary in their portrayal of human resilience amidst life’s uncertainties.

7. Nobody’s Fool (1994)

‘Nobody’s Fool,’ directed by Robert Benton and adapted from Richard Russo’s novel, follows the life of a cantankerous handyman (Paul Newman), as he navigates small-town dynamics and attempts to reconcile with his estranged son. Similar to ‘The Holdovers,’ this film explores the complexities of relationships against the backdrop of a tight-knit community. Both movies capture the transformative power of unexpected connections, portraying characters navigating through personal challenges. While ‘The Holdovers’ focuses on a makeshift Christmas family, ‘Nobody’s Fool’ delves into familial bonds and the protagonist’s journey of self-discovery, making them akin in their portrayal of human nature and the potential for redemption.

6. Finding Forrester (2000)

‘Finding Forrester’ shares thematic parallels with ‘The Holdovers’ as it revolves around an unlikely mentorship. Directed by Gus Van Sant, the film depicts the relationship between a reclusive writer (Sean Connery) and a talented young student. Similarly, in ‘The Holdovers,’ a curmudgeonly teacher forms an unexpected bond with a troubled student over the Christmas break. Both movies explore the transformative power of mentorship, highlighting the impact of these relationships on personal growth and self-discovery. The dynamic between mentor and mentee, coupled with themes of redemption and connection, creates a resonance that unites ‘Finding Forrester’ and ‘The Holdovers.’

5. Charlie Bartlett (2007)

‘Charlie Bartlett’ is a charming comedy-romance for fans of ‘The Holdovers’ due to its exploration of unlikely connections and personal growth. Directed by Jon Poll, the movie follows a wealthy teenager (Anton Yelchin), who becomes an amateur psychiatrist for his high school peers. Much like the endearing Christmas family in ‘The Holdovers,’ ‘Charlie Bartlett’ showcases a diverse cast of characters navigating the challenges of adolescence. The film taps into themes of friendship, mental health, and societal expectations, offering a mix of humor and heartwarming moments. Anton Yelchin’s charismatic performance along with Hope Davis and Kat Dennings adds depth to this coming-of-age tale.

4. The Way, Way Back (2013)

In ‘The Way, Way Back,’ a quirky coming-of-age gem directed by Nat Faxon and Jim Rash, we find echoes of the endearing camaraderie in ‘The Holdovers.’ Duncan (Liam James), spends a transformative summer at a beach town with his mother and her overbearing boyfriend. Much like the unconventional Christmas family in ‘The Holdovers,’ the characters forge unexpected bonds and navigate the nuances of relationships. With its mix of humor, heart, and a stellar cast, including Sam Rockwell and Steve Carell, ‘The Way, Way Back’ captures the essence of unconventional families and the bonding power of shared experiences.

3. Rushmore (1998)

Directed by Wes Anderson, ‘Rushmore’ is a quirky comedy-drama featuring Jason Schwartzman as Max Fischer, a precocious student at Rushmore Academy. The film revolves around Max’s eccentric endeavors, including his friendship with a wealthy industrialist (Bill Murray) and romantic pursuits. Similar to ‘The Holdovers,’ ‘Rushmore’ explores the dynamics of unconventional relationships, capturing the essence of unexpected bonds and personal growth.

Both films showcase characters navigating through unique circumstances, forming unlikely connections that lead to transformative journeys. The shared theme of unconventional families and the impact of diverse relationships make ‘Rushmore’ and ‘The Holdovers’ a cut from the same cloth.

2. Hunt for the Wilderpeople (2016)

Directed by Taika Waititi, ‘Hunt for the Wilderpeople’ is a heartwarming adventure-comedy that follows the journey of a rebellious foster child, Ricky Baker (Julian Dennison), and his reluctant foster uncle (Sam Neill) through the New Zealand bush. Adapted from ‘Barry Crump’ The film beautifully intertwines humor with touching moments, echoing the spirit of unforeseen connections seen in ‘The Holdovers.’ Both films celebrate the forging of unconventional families in unique settings. While ‘The Holdovers’ braves a snowy New England, ‘Hunt for the Wilderpeople’ tackles the untamed wilderness, emphasizing the transformative power of camaraderie and shared adventures in the face of life’s challenges.

1. St. Vincent (2014)

If ‘The Holdovers’ tugged at your heartstrings, ‘St. Vincent‘ is a cinematic gem you won’t want to miss. Directed by Theodore Melfi, this poignant film stars Bill Murray as Vincent, a grumpy and cynical Vietnam War veteran who becomes an unlikely mentor to a young neighbor. Akin to the endearing Christmas family in ‘The Holdovers,’ ‘St. Vincent’ beautifully explores the transformative power of unanticipated connections and relations.

Murray’s stellar performance and the film’s perfect blend of humor and heart create an emotional resonance that mirrors the spirit of ‘The Holdovers.’ It’s a testament to the beauty of finding warmth and redemption in unexpected places, making ‘St. Vincent’ a must-watch for those craving touching, character-driven narratives.

Read More: Where Was The Holdover Filmed?