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.
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.”
“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.”
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#4: Pictionary
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, 2025That 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.
#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.”
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#1: Monopoly
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.”
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
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
? | #NEW Taylor Swift at @questlove’s party playing Uno pic.twitter.com/35xoKOzIip
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Jenga
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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