“Holiday” is a decidedly happy term, although it understandably brings up mixed feelings for some people. The “holiday season” is usually viewed as the time beginning around Thanksgiving and ending around the new year, although some start that window at Halloween and close it at Valentine’s Day.
Another use of the term “holiday” would be in reference to a vacation or period of time off from regular work and chores. Movies have taken full advantage of “holiday” in every sense of the word, and these ten (in order of IMDb rankings), offer a great variety.
10 Holiday Engagement: 6.0
Holiday Engagement (2011) is reminiscent of Melissa Joan Hart’s work in Holiday in Handcuffs and My Fake Fiancé. The movie stars Bonnie Somerville as Hillary and Jordan Bridges as David. Hillary is a journalist whose life falls apart all at once when she loses her job and gets dumped by her careerist fiancé. Hillary’s friend encourages her to hire a date for Thanksgiving with the incentive for the date being a turkey dinner and Hillary’s honeymoon tickets to Mexico.
David wins the job and pretends to be Hillary’s old fiancé, Jason. Shelley Long is hilarious as Hillary’s mom, the hostess of Thanksgiving, and Sam McMurray plays the dad who burns the turkey. Hillary’s sham engagement comes to light when the real Jason comes back, but she realizes she is in love with David, and they get married.
9 Holidate: 6.1
Holidate (2020) meshes “holiday” and “date” to create a unique Netflix Original. Luke Bracey plays Jackson, a bachelor who is no mood to settle down in a serious relationship. Emma Roberts plays Sloane, a twenty-something who is tired of showing up to family functions alone.
After an atrocious Christmas holiday, Jackson and Sloane meet coincidentally at a shopping mall, commiserate over their woes, and decide to be each other’s “holidates,” a decision that takes them through a year full of festive holidays (no strings attached) until they finally realize they’re in love.
8 Holiday In Handcuffs: 6.3
In this hilarious holiday film, Melissa Joan Hart plays Trudie Chandler, an artist whose parents’ disapproval is her constant Christmas tradition. Trudie’s boyfriend dumps her right before he’s supposed to go home for the holidays with her, so she gets creative.
While waitressing, Trudie kidnaps a handsome man named David (played by Mario Lopez) and forces him to pretend to be her boyfriend for the Chandler family’s Christmas in a remote cabin. David and Trudie wind up falling in love after Christmas is said and done; this annual classic is not to be missed.
7 Last Holiday: 6.5
Queen Latifah and LL Cool J are marvelous together in Last Holiday (2006). Queen Latifah plays a saleswoman named Georgia Byrd who finds out she is terminally ill.
She goes on a grand adventure in hopes of making the most of her remaining days, but there might just be a surprise twist at the end. Georgia enjoys traveling, dining, and pampering herself in style, and LL Cool J is the perfect love interest, Sean Matthews. The film is loosely based on a 1950 movie of the same name.
6 The Holiday: 6.9
The Holiday (2006) is a celebrated Nancy Meyers movie (featuring music by Hans Zimmer) with a star-studded cast. Kate Winslet plays Iris, Jude Law is Iris’s brother, Graham, Cameron Diaz plays Amanda, and Jack Black plays Miles, a colleague of Amanda’s ex-boyfriend’s.
Through an online house swap program, Amanda flies to London to spend the holidays in Iris’s home, and Iris flies to Los Angeles to stay at Amanda’s. Both women have been jaded by love recently, but Amanda falls for Graham, and Iris falls for Miles.
5 Every Other Holiday: 7.1
Every Other Holiday (2018) is about a divorced Nashville couple, Rick and Tracie, who are reunited when their two little girls make just one Christmas wish: they want their parents together for the holiday. Rick (David Clayton Rogers) is a bartender and struggling musician, and Tracie (Schuyler Fisk) is getting by working at a local diner. The young parents travel to Tracie’s parents’ home for vacation, putting aside their differences for their girls.
Tracie’s father is a friendly pastor, but her mother is horrible to Rick and does everything she can to push Tracie away from him. Thankfully, it doesn’t work. Tracie and Rick end the movie giving their love another try, and the whole family learns to let them find their own way.
4 Holiday Affair: 7.2
This 1949 classic stars Janet Leigh and Robert Mitchum. Leigh’s character, Connie Ennis, is a war widow employed as a competitive shopper to make ends meet for herself and her son. Robert Mitchum plays Steve Mason, a veteran currently employed at the New York store Connie suspiciously shops at.
Steve hears Connie’s story and decides not to turn her in, which gets him fired. The friendship between Connie and Steve grows into something that could complicate her engagement to another man.
3 Holiday Inn: 7.4
Holiday Inn (1942) is a true Christmas gem of classic cinema. The Irving Berlin musical brings together Bing Crosby, Fred Astaire, Marjorie Reynolds, and Virginia Dale in a love triangle that takes place throughout multiple occasions. Jim (Bing Crosby) uses his theatrical talent to turn an inn into the ultimate stop for any holiday.
The singing, dancing, and romance (not to mention the song “White Christmas”) bring viewers back time and time again.
2 Holiday: 7.8
George Cukor’s Holiday (1938) is a tale of two sisters, Julia (Doris Nolan) and Linda (Katherine Hepburn), and one suitor, Johnny (Cary Grant). Johnny is first set up to be with Julia, but he might be a better match for her more candid and outgoing sister.
Itself a remake of a 1930 film by the same name, Holiday brings out the best of Old Hollywood’s frequent romantic duo, Cary Grant and Katherine Hepburn.
1 Roman Holiday: 8.0
Set in Rome, Italy, Roman Holiday (1953) is a love story between a European princess named Ann (Audrey Hepburn) and an American reporter named Joe Bradley (Gregory Peck).
Joe hopes to get a story on Ann, but everything changes when he falls in love with her on their madcap adventure.
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