Peter Billingsley and Jeff Gillen in A Christmas Story (1983)
Seeing Santa Claus
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A Charlie Brown Christmas (1965)
Picking out a tree
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Will Ferrell and Zooey Deschanel in Elf (2003)
Decorating the tree
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Jimmy Durante, June Foray, Suzanne Davidson, Billy De Wolfe, Paul Frees, Greg Thomas, and Jackie Vernon in Frosty the Snowman (1969)
Waiting for a white Christmas
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Bing Crosby, Danny Kaye, Rosemary Clooney, and Vera-Ellen in White Christmas (1954)
Singing carols
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Nicolas Cage and Makenzie Vega in The Family Man (2000)
Seeing happy and excited children
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Keisha Castle-Hughes and Oscar Isaac in The Nativity Story (2006)
Celebrating the birth of Jesus at a church or religious ceremony (suggested by TsarStepan and jalapenoman)
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"It's A Wonderful Life" Jimmy Stewart, Donna Reed, Thomas Mitchell & Cast 1946 RKO
Being with friends and family
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Vince Vaughn and Reese Witherspoon in Four Christmases (2008)
Vacation to a warm climate (suggested by TsarStepan)
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Ryan Reynolds and Amy Smart in Just Friends (2005)
Vacation to a cold climate (suggested by TsarStepan)
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Steve Carell in The Office (2005)
Christmas parties at work (suggested by TsarStepan)
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Chevy Chase, Beverly D'Angelo, Diane Ladd, Doris Roberts, E.G. Marshall, and John Randolph in Christmas Vacation (1989)
Christmas dinner
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Stan Francis, Burl Ives, Larry D. Mann, Billie Mae Richards, and Paul Soles in Rudolph the Red-Nosed Reindeer (1964)
Watching holiday classics
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Boris Karloff and Dal McKennon in How the Grinch Stole Christmas! (1966)
Making homemade gifts
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Arnold Schwarzenegger in Jingle All the Way (1996)
Buying gifts
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Danny Elfman and Chris Sarandon in The Nightmare Before Christmas (1993)
Waiting for Santa to show up
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Tom Hanks, Nona Gaye, Daryl Sabara, Peter Scolari, Josh Hutcherson, Hayden McFarland, Chantel Valdivieso, and Jimmy Bennett in The Polar Express (2004)
Receiving and opening gifts
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Danny DeVito in Deck the Halls (2006)
Looking at the lights on the houses (suggested by NJtoTX)