7. "Labor Day" (2013)
Kate Winslet and Josh Brolin are fine in this film and are believable together as a couple, but they are not the strongest on-screen duo. Winslet does a great job conveying a pained, fragile single mother, but then again, when isn't she great? "Labor Day" is just okay for us. It's there, and it's really nothing special. For some reason, the movie as a whole feels like it's trying really hard to be something artistic when it's really just another melodramatic love story. This is one of Reitman's weakest entries to his filmography and settles at last place on our list.
6. "Men, Women, & Children" (2014)
The acting is great across the board in "Men, Women, & Children." However, the acting is not enough to elevate it beyond mediocre. We could sit here and talk for hours about what this movie gets wrong, and we feel like Jason Reitman dropped the ball and did the opposite of what he actually wanted to accomplish with this overly ambitious movie. We ended up not really caring about it one way or the other in the end. This is another one of his weaker entries, but it's just interesting enough to edge out the much more formulaic "Labor Day."
5. "Young Adult" (2011)
It's not often that someone creates a story where the audience roots for the main character to fail in their goal. "Young Adult" follows main character, Mavis, as she tries to break up her ex-boyfriend and his current wife (though that isn't the point of the film). It's really a slice-of-life examination of a flawed character who is desperate to reclaim the popularity she received in her youth. It is about a depressed alcoholic who is screaming out for help, but more often than not is met with people who enable her self-destructive behavior because they envy the fact that she is a successful writer who got out of their nothing little town. Jason Reitman directs and Diablo Cody writes this smart but dark satire featuring an incredible performance by Charlize Theron.
4. "Thank You for Smoking" (2005)
"Thank You for Smoking" uses satire and irony supremely well to generate many smartly insightful and humorous moments that hold up well even today. We laugh on the regular each time we watch this film, though it is a more steady stream of small laughs rather big guffaws. This is Reitman's first feature film and he came out of the gate really strong with this one.
3. "Tully" (2018)
Jason Reitman's latest film "Tully" is a darkly comedic character sketch that tries to portray what it's like to be a mother in the modern age. This is not the typical sugarcoated Hollywood version of motherhood. It showcases what it means to be an actual mother with flaws and all. Charlize Theron gives an Oscar-worthy performance as her misery, frustration, and pent-up anger are all massively palpable, as are the love, compassion, and understanding she shows through all the stresses and strains. This film is a return to form for both Reitman and writer Diablo Cody.
2. "Juno" (2007)
"Juno" is a simple yet wonderful, unconventional, smart comedy that makes us laugh out loud throughout the entire thing. Despite being an offbeat comedy, there are many moments of sincerity and tenderness that come off so honest, so brutal, and so touching that we can't help but be emotionally gripped by this film. This best picture nominated movie is so damn good that it came within a hair of topping our list.
1. "Up in the Air" (2009)
This film was very timely the year it came out following the 2008 housing market crash. "Up in the Air" has a lot of wonderfully smart and witty humor throughout its runtime, even though it deals with a very difficult subject to digest. It still winds up being amazingly thoughtful and heartfelt at the same time. It was nominated for six Academy Awards, and though it was, unfortunately, shut out, it is not shut out here, earning the top spot on our list.
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