A Definitive Ranking of ‘The Office’ Christmas Episodes From Most Awkward to Borderline Sad
The Office has seven episodes that center around the Christmas holiday. While all of these episodes hold a special place in the hearts of many fans, we’re here with the definitive ranking of The Office Christmas episodes based on how awkward they are. Find out where your favorite falls on the list.
All Christmas episodes of ‘The Office’ in order
The Office ran for nine seasons, but only seven Christmas-themed episodes exist. Season 1 doesn’t have a Christmas episode because it started in March and only ran for six episodes (the holiday episodes typically aligned with the time of year). Season 4, interrupted by the 2007-2008 Writers Guild of America strike, is also missing a Christmas episode. Here’s every Christmas episode of The Office in order:
- “Christmas Party” (Season 2 — 2005)
- “A Benihana Christmas” (Season 3 — 2006)
- “Moroccan Christmas” (Season 5 — 2008)
- “Secret Santa” (Season 6 — 2009)
- “Classy Christmas” (Season 7 — 2010)
- “Christmas Wishes” (Season 8 — 2011)
- “Dwight Christmas” (Season 9 — 2012)
‘Christmas Party’ episode from season 2 takes the cake for most awkward
This episode takes the top spot in our ranking of the most awkward Office Christmas episode for several reasons. First and foremost, the way Michael handles the “Yankee Swap” gift exchange is top-tier awkward. A $20 limit? No matter for the boss, who instead spends hundreds on an iPod to impress everyone in the office.
On top of Michael’s disapproval of everyone else’s gifts and the tension between Jim (John Krasinski) and Pam (Jenna Fischer) with the iconic tea pot, “Christmas Party” set the bar for future holiday episodes of The Office with subplots and served up even more awkwardness with moments like Meredith (Kate Flannery) getting too drunk and flashing Michael.
The second most-awkward Christmas episode of ‘The Office’ came in season 3
The season 3 episode “A Benihana Christmas” ranks second on our list of most-awkward holiday episodes for one reason: Michael’s Christmas card for Carol (Nancy Carell). After Carol discovers Michael photo-shopped himself into her family holiday card, she breaks up with him. This is the catalyst for the entire episode, which centers around Michael’s heartbreak. Perhaps the best part of this episode is Michael donning his robe — the Christmas gift from corporate — while listening to a sample of James Blunt’s “Goodbye My Lover” repeatedly on iTunes.
‘The Office’ Season 6 episode ‘Secret Santa’ is genuinely hilarious
“Secret Santa” dances on the line of uncomfortably awkward when Michael gets upset about Phyllis (Phyllis Smith) dressing up as the office Santa. Still, this episode contains one of the funniest scenes from the entire series — a scene that caused most of the cast to break while they filmed it. After dressing up as his own version of Santa despite Jim awarding the job to Phyllis, Michael encourages Kevin (Brian Baumgartner) to sit on his lap, resulting in one of the funniest scenes to come out of the series.
‘Dwight Christmas’ isn’t all that awkward at all
Michael Scott’s lack of a presence in the season 9 episode “Dwight Christmas” makes it one of the least awkward episodes in the series. The most uncomfortable moment from this episode has to be when Nellie (Catherine Tate) kisses Toby (Paul Lieberstein). Other than that, “Dwight Christmas” is a fan favorite if only for introducing Dwight’s holiday tradition of Belsnickel. “Are you impish or admirable?”
‘Moroccan Christmas’ is uncomfortable, but not in a fun way
Certain episodes of The Office left fans feeling more discomfort than anything (“Scott’s Tots,” anyone?) The season 5 Christmas episode “Moroccan Christmas” is one of the darker episodes to come out of the series because of Michael’s desire to address Meredith’s alcoholism … at work. However, this is still The Office, which means this episode makes up for that overarching discomfort with a great cold open (Dwight’s gift-wrapped desk) and a B-plot involving Dwight buying up all of the Princess Unicorn dolls in Scranton and selling them for a premium.
‘Classy Christmas’ is another episode that’s more sad than light-hearted and awkward
Unlike previous Christmas episodes of The Office, our hearts break for Michael in the season 7 episode “Classy Christmas.” After finding out Holly (Amy Ryan) is returning to Scranton, Michael goes all out to make the Christmas party one she’ll remember. In doing so, he scraps every plan Pam laid out.
When Michael learns Holly is still with A.J. (Rob Huebel), he’s devastated. Despite dismissing her plans, Pam shows up for Michael in only the way Pam can. She encourages him not to give up on Holly — a heartfelt moment that doesn’t make this episode bad or awkward, but heartbreaking.
‘Christmas Wishes’ is no fun
Another episode missing Michael Scott is the season 8 episode “Christmas Wishes.” This sits at the bottom of our ranking not only because Michael’s missing, but because Andy’s (Ed Helms) desperate need to people please makes us uncomfortable. What’s more, Jim and Dwight get in trouble for too many pranks (is there such a thing?) in this episode, which is no fun at all and therefore why it’s not the best Christmas episode of The Office.
Where does your favorite Christmas episode of The Office rank on the awkward scale? Stream every episode of the comedy series on Peacock.
