The holidays are here and what is usually a time for family, food, fun can quickly turn into utter chaos. This week’s watchlist highlights the awkward reunions, over-the-top decorations, and even unexpected guests that erupts from spending the season with loved ones.

Whether it’s a disastrous mission to get home for Thanksgiving in Planes, Trains and Automobiles, loneliness and found family in The Holdovers, a chaotic family reunion in This Christmas, or a magical competition in Candy Cane Lane, each of these films reminds us that no holiday is perfect – but it can still be unforgettable. Packed with eccentric relatives, clashing personalities, and moments of sweet and tender connection, these movies blend comedy and drama in just the right proportions. They really prove that, no matter how messy or crazy the holidays get, the bonds of family, friends, and even strangers – remain at the heart of the celebration.

The Holdovers

Two women are animatedly interacting, one holding a wooden hand and the other holding a red object, amidst a backdrop of various colorful items and props.
The cast of The Holdovers / Photo / Focus Features

A grumpy boarding school teacher is forced to stay on campus over Christmas break to supervise the “holdover” students with nowhere else to go. Among them is Angus Tully, a teen dealing with familial turmoil, and Mary Lamb, the school’s head cook who recently lost her son. The unlikely trio spend the holiday together as their loneliness and guardedness slowly give way to understanding and a sense of found family.

Director: Alexander Payne / Starring: Paul Giamatti, Da’Vine Joy Randolph, Dominic Sessa

Friendsgiving

Two women excitedly interacting while holding unique objects in a vibrant outdoor setting filled with various items, suggesting a lively or playful moment.
Aisha Tyler & Malin Åkerman in Friendsgiving / Photo / Saban Films

Molly and Abbey are two best friends hoping for a quiet, low-key Thanksgiving after a year of personal upheaval. Their plans unravel when an assortment of friends, strangers, exes, and unexpected guests descend on Molly’s home, turning the holiday into a chaotic whirlwind.

Director: Nicol Paone / Starring: Malin Åkerman, Kat Dennings, Aisha Tyler

This Christmas

A large group of diverse individuals stands together on the steps of a home, surrounded by colorful flowers. They appear to be posing for a family photo, smiling and displaying a sense of togetherness.
Cast of This Christmas / Photo / Sony Pictures Entertainment

This Christmas follows the Whitfield family as they reunite under one roof for the first time in years, bringing with them secrets, tensions, and long-simmering sibling rivalries. As the holiday unfolds, each family member confronts personal struggles—from relationship turmoil to career crossroads—forcing them to reckon with what truly matters. Despite the chaos, humor, and emotional blow-ups, the Whitfields rediscover their bond and the joy of being together. The film blends comedy, romance, and heartfelt drama into a warm, lively holiday ensemble piece.

Director: Preston A. Whitmore II / Starring: Regina King, Idris Elba, Loretta Devine, Chris Brown, Columbus Short

Planes, Trains and Automobiles

Two men walking down a snowy road, one in a suit carrying a small suitcase and the other in a blue coat with a large, bulky trunk.
Steve Martin & John Candy in Planes, Trains and Automobiles / Photo / Paramount Pictures

Neal Page is an uptight marketing executive desperate to get home to his family for Thanksgiving. His trip is derailed at every turn, forcing him to team up with an overly talkative yet well-meaning salesman. Neal is dragged through a chaotic, cross-country trip of canceled flights, broken-down trains, and roadside misadventures.

Director: John Hughes / Starring: Steve Martin, John Candy

The Family Stone

A family gathers for a group photo in a cozy living room decorated for the holidays, featuring a mixture of adults and children with varying expressions of joy and anticipation.
Cast of The Family Stone / Photo / 20th Century Fox

When Everett Stone brings his girlfriend home for Christmas to meet his family, chaos and several misunderstandings ensue. A simple holiday gathering exposes unspoken resentments and unexpected romantic entanglements into a storm of dysfunction.

Director: Thomas Bezucha / Starring: Sarah Jessica Parker, Dermot Mulroney, Diane Keaton, Luke Wilson, Rachel McAdams

The Best Man Holiday

Four men dressed in shiny black suits and hats perform a synchronized dance in a festive setting decorated with Christmas trees and holiday gifts.
Taye Diggs, Morris Chestnut, Harold Perrineau, & Terrence Howard in The Best Man Holiday / Photo / Universal Pictures

A sequel to The Best Man, the group is reunited over Christmas after years apart. What begins as a festive holiday weekend quickly becomes emotionally charged as old rivalries, buried secrets, and unresolved tensions resurface.

Director: Malcolm D. Lee / Starring: Morris Chestnut, Taye Diggs, Nia Long, Sanaa Lathan, Regina Hall

Four Christmases

A woman and a man in a conversation at a doorway decorated with a Christmas wreath, displaying warm expressions.
Reese Witherspoon & Vince Vaughn in Four Christmases / Photo / Warner Bros.

A happily unmarried couple plans for a tropical holiday getaway, but with their flight cancelled, they are forced to spend Christmas visiting each of their four divorced parents.

Director: Seth Gordon / Starring: Reese Witherspoon, Vince Vaughn

Candy Cane Lane

A diverse group of people, including children and adults, stands together on a festive street decorated with colorful holiday lights. They are smiling and waving, embodying a joyful holiday spirit.
Cast of Candy Cane Lane / Photo / Prime Video

Chris Carver is a devoted dad determined to win his neighborhood’s annual Christmas home-decorating contest. When he unintentionally makes a deal with a mischievous elf, the competition spirals into chaos. As Christmas Eve fast-approaches, Chris and his family race to undo the elf’s spell before their entire town is turned upside down.

Director: Reginald Hudlin / Starring: Eddie Murphy, Tracee Ellis Ross

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