The group chat says “game night,” the snacks are handled, and now you’re staring at your shelf like: what are the best classic board games for Christmas that won’t derail the whole vibe?
If anyone knows what kind of entertainment belongs at the holiday table, it’s Phil Orbanes — a legendary board game designer and historian, founding partner of Winning Moves Games, former Parker Brothers exec, and recent Lifetime Achievement Award recipient from the toy and game industry.
During the Monday, December 15 episode of Nostalgia Tonight, the 78-year-old Monopoly expert joined host Joe Sibilia to share his “top five nostalgic board game recommendations for the family to play at Christmas.”
Before he ranked anything, Orbanes made one thing clear: the whole point is picking games people already know (or can learn in seconds), not something that requires a 30-minute rules lecture. “The most important word that you used in your question to me was classic,” Orbanes said, because it means “what games do people know and, you know, hopefully love… and they don’t need to learn to play according to a new set of rules.”
With that in mind, here’s his holiday ranking — plus his “easy-to-play” bonus list.
“I would rank Scrabble as number five,” Orbanes said, noting that while it’s hugely popular, it does require “a knack for vocabulary” and “a knack for the written word.”
It’s a great competitive game, he explained, but not everyone wants to flex their spelling skills at Christmas dinner. Scrabble works best when the table is in the mood to slow down a bit, think things through, and side-eye each other over questionable words.
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#4: Pictionary
“I think in the fourth spot, I would put Pictionary,” Orbanes said, because the goal is simple: draw the idea even if it looks terrible. “It doesn’t matter how crude, it just needs to communicate what it is that you’re drawing.”
That’s what makes it work. You don’t need artistic talent, just enough confidence to try. Compared to Scrabble, he said, “it's not quite as intimidating, if you will, as having a command of English.”
In 1985, ‘Pictionary,’ invented by Robert Angel, was released pic.twitter.com/lrbxJK6c53
— RetroNewsNow (@RetroNewsNow) November 18, 2025Charades-style games took the number three spot. According to Orbanes, “Anything that has a charade-like quality where you're, you know, where you're acting out a word or a concept is always a favorite.”
That can mean classic Charades, or modern party games like Heads Up!, Catch Phrase, or any game that gets people on their feet and acting things out.
“It’s not too difficult to play a charades type of game because you are expressing yourself to get an idea across,” Orbanes added. “And it’s funny to see how people do this.”
#2: Clue
“Number two, I think, would be Clue,” Orbanes said, explaining that “the classic detective game” works so well because “everybody is involved on every turn.”
He described it as a whodunit that keeps things moving without feeling dull. “It’s not very complicated,” Orbanes added. “It’s a process of elimination.” You can play it casually and still have fun, or lean into strategy if that’s your thing. Either way, the entire table stays locked in.
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#1: Monopoly
Taking the number one spot is Monopoly. Orbanes calls it “the number one social interactive game in the world,” saying the real appeal goes far beyond the board itself. “Whenever you play Monopoly, you learn a great deal about all of your opponents by the way they speak and act and interact with you,” he said.
After decades spent watching even the best players compete at tournaments, Orbanes believes the most memorable part of the game isn’t the money or the final outcome. “It’s what happens off the game board in Monopoly that is the best reward,” he explained. “It’s not necessarily having the most money and perhaps bankrupting everybody. It’s what you experience with whoever is around the board.”
That social element, he added, is a big reason the game has endured for nearly 90 years and why it still feels just as relevant today as it did in 1935.
On "Nostalgia Tonight with Joe Sibilia," Board Game Expert, Historian, and Designer Phil Orbanes of @WinningMovesUSA told me his four secrets to increasing your odds of winning Monopoly! Listen to the full interview here: t.co/1abANserIy pic.twitter.com/eOGsLbDKZx
— Joe Sibilia (@thejoesibilia) December 15, 2025Easy-to-Play Holiday Games That Keep Things Light
After sharing his top five classics, Orbanes offered a second category for holiday tables that want fun without the commitment. “This next category… is what I would call either easy to play or easy to engage with games,” he said. These picks are lighter, just as enjoyable, and don’t require much setup or explanation.
First up: Guess Who. The classic face-guessing game might be aimed at 10-to-12-year-olds, but Orbanes insists it's "equally fun for anybody in the family." The game is totally self-contained — plastic characters that flip up and down on little pivots — which makes setup and cleanup a breeze.
Uno
Then there's Uno, which Orbanes calls "probably the world's most popular card game." He's not wrong — celebrities from Taylor Swift to the Obama family have been spotted playing it. "I think everybody knows how to play Uno," he said. "If you have a deck of Uno cards, it's a cinch that it's going to be a fun, entertaining game to play without hesitation."
? | #NEW Taylor Swift at @questlove’s party playing Uno pic.twitter.com/35xoKOzIip
— Taylor Swift News (@TSwiftNZ) July 13, 2023His third pick might surprise you: Rack-O. It's been around for about 70 years, but it flies under the radar compared to flashier games. The premise is simple — you have a rack of numbered cards and need to arrange them in numerical order by drawing and discarding. "It's a very quiet game," Orbanes said. "But it has an enormous popularity among people who really don't want the tension and the, if you will, the uncertainty of, let's say, Monopoly."
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Jenga
Jenga also made the list, because who doesn't love the suspense of a teetering tower? "Everybody loves the idea of building this wooden tower and then removing blocks from it and putting it on top of the tower until finally it becomes unstable and falls," he said. "There's no doubt of who has caused that to happen. So the ending is very conclusive." Plus, it's easy to reset and go again.
Card Games
And finally, Orbanes reminded listeners not to overlook good old-fashioned card games. "If your family or your group of friends has a favorite card game, Christmas is a great time to play it," he said. "Whether it's Hearts, or maybe it's Pinochle, maybe even Bridge, the whole idea of card games is it brings several people together. They socialize continually as they're playing the cards. And that's what you want.”
So whether your family is all-in on Monopoly, debating words in Scrabble, or just looking for something easy to pull out after dinner, Orbanes’ advice comes down to one thing: pick games people already know and enjoy being around each other while they play. The rules matter less than the memories — and that’s what keeps these classics coming back every Christmas.
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