2 Movies 1 Moment: ‘We’re the Millers’ Versus ‘When Harry Met Sally’

Time for 2 Movies 1 Moment, and in this edition, it’s a battle between the classic romantic comedy When Harry Met Sally and the recent road trip comedy We’re The Millers.

Experiencing a surge in popularity these days, partly due to its frequent use on The Tonight Show with Jimmy Fallon, the party game Pictionary is the focus of our 2 Movies 1 Moment this week, a game invented way back in 1985, and one that hasn’t exactly had a lot of exposure in the movies, but does show up occasionally, most often in comedies. A game of art skills and communication, it’s not always easy to play, and makes for some real laughs, in real life and in the movies. But which one does it best? Let’s compare.


We’re the Millers (2013)

THE FILM: When a small-time pot dealer is robbed, he’s forced by his boss to head to Mexico and pick up large load of marijuana. To make it easier to cross the border, he hires a fake family to travel with him in a huge motorhome. Initially at each other’s throats, the foursome soon to get along and come together like a real family.

Pictionary
We’re The Millers, 2013 © Warner Bros. Pictures

THE PICTIONARY MOMENT: Masquerading as a husband and wife, David (Jason Sudeikis) and Rose (Jennifer Aniston) bring along a dorky kid named Kenny (Will Poulter) and a troubled teen girl named Casey (Emma Roberts) to pose as their kids. Having to park at camper sites, they end up meeting other motorhome enthusiasts, including the Fitzgeralds (Nick Offerman and Kathryn Hahn). One evening, the two families sit outside and begin a game of Pictionary, with Kenny taking to the sketchpad while his “parents” try to guess. It doesn’t go so well.

Pictionary
We’re The Millers, 2013 © Warner Bros. Pictures

Kenny’s drawing skills are not quite developed and he ends up doodling a long dark rod-shaped image with circular lines at the base. David takes a few stabs at guessing but it’s Rose who thinks she’s got it solved, clearly seeing something everyone else does not. Spouting out “penis” first, she quickly blurts some euphemisms and, since the marker is black, a gender specific one at that, ending with the movie reference “Black C*ck Down.” She’s a bit off. Kenny says it’s a skateboard.

Pictionary
We’re The Millers, 2013 © Warner Bros. Pictures

Perhaps the most interesting thing about this, aside from Kenny’s stupendously awful drawing skills, is that this is not even Aniston’s first Pictionary movie moment. Back in 2006, she starred with Vince Vaughn in the romantic comedy, The Break-Up, where she also participated in a Pictionary party game, though minus the pornographic overtones.

Pictionary
The Break-Up, 2006 © Universal Pictures

But we’ll stick with We’re The Millers for this battle and put all the stock in Aniston for why it works. Spending most of her career as a television good girl, Aniston took to the movies to change that perception, and none more so than this raucous comedy where she curses and strips her way into our hearts. In this scene, she flat out gets the biggest laugh, her character forgetting that she’s supposed be a wholesome mother, seeing what she sees and saying so loud and proud. And let’s be honest, it kinda really is what Kenny drew. It’s a great Pictionary moment, but is it better than…


When Harry Met Sally (1989)

THE FILM: Harry (Billy Crystal) meets Sally (Meg Ryan) on a ride-share trip from Chicago to New York City after graduating from college. Over the next ten years, they occasionally bump into each other while in various stages of problematic relationships and slowly begin to realize they might be perfect for each other.

Pictionary
When Harry Met Sally, 1989 © Columbia Pictures

THE PICTIONARY MOMENT: The thing about Harry and Sally is that for a long time, they don’t quite get that their remarkable friendship is a good sign that they should be dating, but they both seem blind to the obvious, instead setting each other up with other people (who end up becoming a couple of their own). At a party one night with that couple, Jess (Bruno Kirby) and Marie (Carrie Fisher), Harry brings a date and Sally is with hers, though neither are that serious, and are clearly still thinking of the other. As a game of Pictionary starts, Sally begins to draw and the others, including Harry and Jess, try to guess.

Pictionary
When Harry Met Sally, 1989 © Columbia Pictures

Sally, as expected, is not so good at drawing, but more so, Harry and Jess are worse at guessing. As she seems to doodle the shape of a baby and then a pair of lips and a series of strenuously illustrated lines, Jess takes a stab, declaring with certainty that she is drawing none other than, wait for it, a “Baby Fish Mouth” because obviously she is. She is not. The look she gives him makes that clear.

Pictionary
When Harry Met Sally, 1989 © Columbia Pictures

No one guesses it right and the timer dings, leaving her having to explain her work. While the scene is meant to put Harry and Sally in the same room and build tension about their attraction, it is Jess who steals the scene. Kirby straight-up robs the entire cast of the comedy and walks away with what might arguably be the funniest line in the movie . . . well, second funniest. “I’ll have what she’s having,” wins that prize. Either way, it’s all about the timing here, and the scene has a wonderful spontaneity to it that feels unscripted. Resisting the obvious temptation to use innuendo, the drawing is instead secondary to the joke and it’s all about the characters rather than the setup. It’s a classic Pictionary moment. So which is the better?


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2 Comments

  1. Jay January 24, 2017
    • David Duprey January 24, 2017