Starring: Colin Farrell, Scott Caan, Ali Larter, Gabriel Macht, Kathy Bates, Will McCormack, Timothy Dalton

Director: Les Mayfield
Released: 2001

Mood: If work has been exhausting and you can’t handle the news and just want to shut off your brain with stupid fun but you already watched Young Guns.

It’s so weird to me that I started this review with no idea what to say about American Outlaws. Like Maverick and Tombstone, I’ve watched this movie a gazillion times. 

If you think that says something about my taste, you are 100% correct.

American Outlaws is a story about the James-Younger gang. And I do mean a STORY – other than the names of the characters, there’s almost zero historical accuracy. But are you watching a Colin Farrell movie to study for a history test? I think not. 

If you want something closer to the truth, watch The Long Riders. If you need a stupid-fun action comedy to break up a miserable week, this is your movie. 

Like many other Westerns, American Outlaws opens on a Civil War battlefield. It’s a great way to quickly showcase traits like bravery, cowardice, and villainy, and set the tone for the rest of the movie. 

All of the main characters are fighting for the South. Right away, you have sort of suspend reality to enjoy this version’s easygoing charm. The real James-Younger Gang members fought REALLY hard for the South. Read up on it – they did some bad, murder-y shit.  

In the movie, Jesse James (Colin Farrell) demonstrates his cocky bravery by leaping over a blockade and galloping full-tilt across the field, so the always-chill Frank James (Gabriel Macht) can take out the Gatling gunners while everyone is distracted.

Immediately afterward, they find out the war is over and head home to their farms. Kathy Bates plays Ma James, with a flawless blend of fussy mama bear meets fierce pioneer woman. This movie definitely could have used more Kathy Bates. She’s perfect for the strong, wisecracking woman in modern Westerns. She’d have been a great addition to Godless.

The boys and their families are threatened by Thaddeus Rains (Harris Yulin) and his team of rich white guys, trying to kick them off their land and use it to expand the railroad. The James and Younger boys form a gang and ride around robbing banks that store the railroad’s money.

And they do it all without missing a beat in their silly banter.

Let’s talk about the witty dialogue of American Outlaws. It’s so ’00s and it’s actually really funny. 

• “You got big. I mean, you aged. What I mean is in a good way you got big and older.” – Jesse to Zee (Ali Larter)
• “Cole lost his temper.” “Oh no.” “Well, he just lost his temper a little!” “How many of ’em did he kill, Bob?” – Bob Younger (Will McCormack) to Frank 
• “Some Indian tracker you turned out to be, Tom.” “You paid me to find you Bluecoats, there they are.” – Cole (Scott Caan) and Comanche Tom (Nathaniel Arcand) upon being ambushed by Union soldiers
• “Just because he reads all them books and he knows all them big words don’t make him smart!” “Uh, yeah it does.” – Cole to Bob Younger, regarding Frank’s book smarts
• “Well, say we burst into a bank and we go, ‘We’re the Younger-James gang!’ Now people are gonna be thinkin’, ‘The younger James gang? Is there an older James gang? How come we never heard of the older James gang?’ So people are tryin’ to figure that out instead of raisin’ their arms.” – Bob Younger’s brilliant logic

Leading the charge against the James-Younger gang is Allan Pinkerton (Timothy Dalton): Scottish detective, spy, and badass founder of the Pinkerton National Detective Agency, which still exists today. 

Dalton’s ferocity is almost out of place in American Outlaws – almost. He’s the ideal adversary to balance the posse of jolly scamps, even though this version made him weirdly respectful of Jesse. In real life Pinkerton never successfully caught Jesse James, but he definitely never told him he’d be safe in Tennessee. As if the OG Pinkerton would just let Jesse F*cking James retire in peace. 

Basically everyone else did a good job in American Outlaws. I use ‘good’ in relation to what kind of movie this is – I’m not comparing them to the f*cking Carradines or anything, just to each other in this movie.

Gabriel Macht is so solid and seemingly natural as Frank James that I was all over IMDB, hoping to find him in more Westerns. I was disappointed to find a surprisingly sparse filmography that includes Beverly Hills, 90210 and Sex and the City.

I enjoy Scott Caan in everything I’ve seen, particularly the Ocean’s movies. American Outlaws was the first place I saw him and the reason I bought the DVD – because his face is on the cover and he looks EXACTLY like my little brother and it freaked me out. After I showed my brother his doppelgänger, he actually convinced someone at college that he was in Ocean’s Eleven. 

True story.

The whole vibe of the movie is kind of a party. It’s got that mix of modern music and old-timey costumes that was popular in the early ’00s, notably in movies like A Knight’s Tale and Romeo and Juliet (the Leo version). It’s highly reminiscent of Young Guns, with the rock music and not-so-subtle theme of attractive actors being attractive.

I know I’m WAY too forgiving of this movie, especially for one without a single noteworthy moustache. I’ve ripped on other Westerns for f*cking around too much with historical accuracy, or for having a “too modern” feel. Maybe it’s because I’m not fully convinced that Scott Caan isn’t actually my brother.

Not every Western has to be an Oscar hopeful – although a SHOCKING number have been nominated! I guess American Outlaws just checks all my boxes for weeknight entertainment: fun, fast, doesn’t make you think too hard, and has lots of great shootouts. The end.