The Top 25 Most Underrated Heist Films

This week brings the latest film from Brad Pitt, “Killing Them Softly,” a film about a heist gone wrong- which in movies is typically the case- though not always. With that release on the horizon, I thought I’d take a look at some of the more underrated heist-themed films out there.

Keep in mind this is in no way intended as an “essential” list, so don’t go looking for outright classics like “Dog Day Afternoon,” “Reservoir Dogs,” “The Killing” and “The Taking of Pelham
1-2-3,” or even pseudo-classic guilty pleasures like “Point Break”- it’s not that kind of list. Instead, I thought I’d bring attention to the lesser-known offerings out there, for those looking for something a bit more off the radar. Be sure to chime in with your faves in the comment section!

25. The Perfect Score (2004)

A film featuring a cast that went on to much bigger things, this teen comedy benefits enormously from its quirky set-up, in which the thing being heisted isn’t money or jewels or what have you- but test scores. With their SAT scores on the line, a group of teens band together to infiltrate the ETS and change their scores, in a unique twist on the tried-and-true subgenre. The cast includes a young, scrappy Scarlett Johansson, then-future Human Torch and Captain America Chris Evans, and sexy “Parenthood” TV-star Erika Christensen, who also cropped up in the heist-gone-wrong flick “How to Rob a Bank,” which is worth a look as well. Critics hated it, calling it “The Breakfast Club” gone horribly wrong, but I think it’s perfect afternoon cable viewing worth looking out for, especially if you like the cast. (For similar holiday-themed viewing, I somehow always find myself watching “A Holiday Heist,” but that may well be because of my long-standing crush on Lacey Chabert, so take that with a grain of salt.)

24. Hudson Hawk (1991)

People hated this film when it came out, especially critics, who felt that it was the epitome of Bruce Willis’ fame having gone entirely too far, after the enormous success of the “Die Hard” films. Willis himself co-wrote the story, with a script co-written by Daniel Waters and directed by Michael Lehmann, then-hot after the cult success “Heathers.” (Fair warning: it’s nothing whatsoever like that classic, to say the least!) Unwisely promoted as an action film, it’s actually a satire of action films that is very heavy on over-the-top campy slapstick performances that often veer into cartoonish territory. In short, it’s a love-it-or-hate-it affair that most hated, but which I kinda liked almost in spite of itself. To be sure, Willis is pretty cloying here, but his chemistry with co-star Danny Aiello (who was never more likeable than he was here, as he typically played the heavy) is palatable and engaging, and the camp-tastic villains played by Richard E. Grant and Sandra Bernhard are worth the price of admission, IMHO. Also cropping up are “CSI: Miami”-star David Caruso in an early role, plus Andie MacDowell and James Coburn. If you liked the more self-referential-era “Moonlighting” episodes that regularly broke the so-called “fourth wall,” you’ll probably like this- but you’ll know pretty early on, regardless, if it’s your kind of thing or not.

23. Harlem Nights (1989)

Another critically-lambasted flick, this was one of the last old-school raunchy films Eddie Murphy made- the other being the equally reviled and also better-than-you-remembered “Boomerang”- before turning to more family friendly material. Though admittedly never as funny as you hoped it would be given the cast, it’s still a lot of fun, especially if you’re a fan of anyone involved. Check out this line-up: Richard Pryor, Redd Foxx, Arsenio Hall, Robin Harris, Danny Aiello, Michael Lerner, Della Reese, Lela Rochon and Jasmine Guy. Not too shabby. It was a huge hit, but doesn’t tend to come up when Murphy’s best flicks are talked about. That’s too bad, because I laughed my ass off. To me, this was what “Idlewild” was sort of going for, only much more fun.

22. Candleshoe (1977)

You know how you love certain films when you’re a kid and then you get older and find out that most everyone critic-wise hates them, but you still kind of do? (Kind of like, I don’t know, most of this list so far?) This is another of those kinds of films. My father raised me on a steady diet of Disney, and I still love this flick with a young Jodie Foster as a street kid/hustler that is recruited to impersonate a missing heiress and snoop around for supposedly hidden treasure. Turns out the lady of the house (Helen Hayes), completely unbeknownst to her, is flat broke and in dire danger of losing her home, palatial though it may be. Helping to keep her in the dark is dapper David Niven, playing a variety of roles amongst the non-existent staff. I just loved the mystery element here and all the clues that led to the missing treasure, and the idea of living in a mansion as a middle-class kid really appealed to me. It’s kind of slight, I suppose, but I still love this one dearly, and Foster’s movies of this period, which also include “Bugsy Malone” and “Freaky Friday,” are among my fave kid movies. Fun fact: The titular house was also used as the setting of TV’s “Silver Spoons.”

21. Welcome to Collinwood (2002)

Everyone knows the “Ocean’s” films, but considerably less know about this little gem, also starring George Clooney and produced by director Steven Soderbergh. For my money, it may not be as flashy as any given film in that series, but is a lot less annoying and cloying. You make a movie like “Ocean’s” for the locale and the paycheck- you make a film like this because you really have a solid story to tell. The cast is equally excellent in its own way, too, with William H. Macy, Sam Rockwell, Patricia Clarkson, Gabrielle Union, Jennifer Esposito, Isaiah Washington, Luis Guzman, and Michael Jeter. Don’t get me wrong, this is a pretty low-key, very low-budget labor of love from directors Anthony and Joe Russo, who went onto to do the Emmy-winning pilot for “Arrested Development,” which established the influential look of that show. They also work on such beloved cult shows like “Community” and Happy Endings.” Smaller doesn’t have to mean bad by any means, and if you like any of those shows, you’ll probably appreciate this fun bit of business, even if it never quite achieves true “classic” status. Who says all films have to?

20. Johnny Handsome (1989)

Younger generations that know Mickey Rourke for his work in films like “Sin City” and “The Wrestler” may not be aware of what a huge star he was back in the day- or how different he looked. Ironically, in light of the massive damage since inflicted on the star’s face over the years during his boxing stint, this film takes on an all-new subtext the filmmakers could never have predicted back then. Rourke plays a disfigured man who undergoes radical plastic surgery to change his looks, making the titular taunt an actual reality, and helping him land the sexy Ellen Barkin, who knows a thing or two about reconfiguring herself as well. A flop at the time, the noir-influenced film co-stars the always-engaging Morgan Freeman and Forest Whittaker, plus solid character actors Lance Henriksen, Scott Wilson (“The Walking Dead”) and Elizabeth McGovern. It’s directed by underrated director Walter Hill, best known for “The Warriors” and “48 Hours,” but also behind the classic heist film “The Getaway” with the legendary Steve McQueen. This one isn’t up to those lofty standards, but its well worth a look, especially if you like that cast.

19. Quick Change (1990)

One of the lesser-known films in Bill Murray’s canon, “Quick Change,” which he co-directed (his only directing credit to date), is about a heist gone right. However, it’s the getaway that goes horribly awry, leading to a comedy of errors that just keeps building up as the crew does their damnedest just to get the hell out of dodge- or rather, Manhattan. It’s not LOL-funny, to be frank, but it is solidly entertaining, with a great cast that includes Jason Robards, Geena Davis, Randy Quaid, Stanley Tucci, Phil Hartman, and a hilarious Tony Shalhoub (“Monk”) as a cab driver who doesn’t understand a word of English, which doesn’t help matters. The film would make for a nifty double feature with Martin Scorsese’s similarly low-key and themed “After Hours.” It also features a terrifically dry performance from Murray that directly foreshadows his then-future and subsequently much-acclaimed work in “Lost in Translation” and “Broken Flowers.”

18. Sugar & Spice (2001)

This is a cute teen-themed movie that is kind of to heist films what “Scream” was to slasher flicks: that is to say, very tongue-in-cheek and self aware. Check out the scene where the group of girls prepares to rob a bank by.watching other heist films, like “Point Break” and “Reservoir Dogs.” It also features a great cast of mostly should-have been stars, including Marley Shelton (who later cropped up in a great role in “Grindhouse: Planet Terror”), Melissa George (currently on “Hunted”), Alexandra Holden (“Rizzoli & Isles”), Rachel Blanchard (TV’s “Clueless”), and Marla Sokoloff (“The Practice”). The names here are Mena Suvari (“American Pie” and lots of other movies with “American” in the title) and James Marsden (“X-Men”), plus great cameos from Conan O’Brien, Jerry Springer, and MTV’s Kurt Loder as themselves. If a movie about cheerleaders turning to a life of crime is wrong, I don’t want to be right.

17. Bottle Rocket (1996)

The debut film from critically-acclaimed director Wes Anderson, of “The Royal Tenenbaums” and “Moonrise Kingdom” fame, this is far and away his least-known film- and arguably his most atypical. Lacking the novel-on-film approach of his better-known work, this more subtle film was also the debut of brothers Luke and Owen Wilson (who co-wrote with Anderson) and shot on location in the threesome’s native Texas. James Caan and Leslie Mann also crop up in this neat indie that may not appeal to hardcore Anderson or Wilson brother fans, but if you like character studies, this will be right up your alley. Further, if you flat-out don’t like their stuff under normal circumstances, this might just do the trick for you where the others don’t. It may be the least-celebrated of the Anderson oeuvre, but I think it holds its own just fine and is well worth a look.

16. Bound (1996)

Another lesser-known effort from directors better-known for other things, this film marked the debut of the then-unknown Wachowski Brothers, who would go on to greener pastures with the “Matrix” trilogy and, more recently, “Cloud Atlas”- not to mention a sizeable change of another sort in the case of one of the brothers, to say the least! In some ways, this film could be seen as a harbinger of things to come for one of the brothers, Laurence, who went onto have a sex change and become Lana. The film explores female sexuality in a frank and sometimes explicit way, with one of the main characters a lesbian ex-con (Gina Gershon) and the other bi-sexual (Jennifer Tilly) who longs to escape a violent relationship with a Mafia thug (Joe Pantoliano). It’s a novel twist on the typically male-dominated crime genre, and well worth seeing, even if the “Matrix” films aren’t your cup of tea. Fun fact: the sex scenes were “overseen” by noted sex therapist/feminist Susie Bright.

15. St. Trinian’s (2007)

Another teen-centric entry, this one revolves around the titular all-girls’ boarding school, which is the antithesis of a proper English college and pretty much wall-to-wall with misfits and troublemakers. Despite this potentially scandalous material, the cast is first-rate, including Oscar winner Colin Firth (“The King’s Speech”), Rupert Everett (in drag as the headmistress), comedian Russell Brand, Bond girl Gemma Arterton, erstwhile-“Sarah Connor” Lena Headey (also of “Game of Thrones”), Mischa Barton (“The O.C.”), Juno Temple (“The Dark Knight Rises”), Lucy Punch (“Ben & Kate”) and an appealing leading lady in Talulah Riley (“Pride & Prejudice”). Other Brit luminaries crop up in supporting roles, and there’s also a cameo from English sirens Girls Aloud. It’s a lot of fun and trashier than you might have thought Brits were capable of, Benny Hill notwithstanding. If you like this, there’s a sequel as well, with most of the cast returning for a second-go-round, even Firth, post-Oscar win. Who could blame him, with that cast?

14. The Bank Job (2008)

Another from the Brits, this one features go-to action guy Jason Statham in one of his more understated performances- which is to say, one in which he actually stops to take a breath once in a while and does some bona fide acting. (See also #4- sort of.) Based on a true story, this period piece takes place in 1971 and concerns a robbery on the famed Baker Street, in which the money and items stolen were never recovered. In other words, it’s one of the heist films where they actually get away with it. That’s no spoiler, as getting there is half the fun. Sexy Saffron Burrows (“Law & Order: Criminal Intent”) is on hand as well, as a model with some inside info on the bank at hand. What this film lacks in star power (at least in the States), it makes up for in period detail, music, and overall atmosphere. A truly underrated gem of a film for those who like their heists down and dirty.

13. Normal Life (1996)

No one ever talks about this, arguably one of Ashley Judd’s very best performances, right up there with the equally underrated “Ruby in Paradise.” She plays an emotionally wrecked individual that falls for a cop (Luke Perry, but don’t let that scare you away: he’s never been better) and tries to lead a “normal life”- hence the title. A hopelessly-addicted drug and alcohol user, her lifestyle is decidedly at odds with his and trouble ensues, eventually leading to him getting fired and turning to a life of crime, which she excitedly joins in on, Bonnie & Clyde-style. Based on a true story, the movie also features sexy redheaded “Private Practice”-vet Kate Walsh in an early turn. If you go out of your way to see one film on this list, make it this one: if you can find it! It’s worth the effort.

12. The Way of the Gun (2000)

As raucous and over-the-top a film as you’re likely to ever see, this one is not for the faint of heart. Written by a frustrated Christopher McQuarrie after his efforts to get a film made after winning an Oscar for writing “The Usual Suspects” proved unfruitful, this film was the result after friend and leading man Benicio Del Toro encouraged him to make another crime film on his own terms. Though he toned down the content a bit over time, the film remains pretty no-holds-barred from the get-go, as a hilariously foul-mouthed Sarah Silverman- a long way from “Wreck-It Ralph”- berates a guy and all hell subsequently breaks loose, rarely letting up, especially in elaborate shoot-out sequences choreographed by McQuarrie’s former Navy SEAL brother. The plot involves a kidnapping of a pregnant surrogate (Juliette Lewis) by Toro and co-star Ryan Phillippe and subsequent action involving her bodyguards (Taye Diggs and Nicky Katt), the baby’s father (Scott Wilson again), and his best pal, played by James Caan, in a stand-out performance in a film full of them. Things get pretty bloody, and the language is, shall we say, pretty colorful, so this won’t be for all tastes. If you’re a Tarantino fan, though, this should be right up your alley.

11. The 51st State (aka Formula 51) (2001)

Another critically-reviled film, I kinda liked this fun spin on the heist thriller with a loopy plot that involves a designer drug-making chemist played by Samuel L. Jackson who double-crosses his American connect (Meat Loaf!) to head to England to hawk his wares. Things go awry and the connect survives and sends a contract killer to get rid of Jackson, played by a never-sexier Emily Mortimer, looking like she’s auditioning for the latest “Underworld” flick. Meanwhile, Jackson meets up with go-between Robert Carlyle (TV’s “Once Upon a Time”) to sell his formula, hence the title. The connect decides he needs Jackson so that he can replicate the formula and orders Mortimer to kill anyone he tries to sell it to. Mayhem ensues, involving any number of colorful characters and scenarios, including skinheads, a rave, an Animal Testing Facility, Rhys Ifans, and a climatic soccer match- make that “football”- this is England, after all. It’s directed by the legendary Chinese director Ronny Yu (“The Bride with White Hair”), the soundtrack is fab, the Liverpool locale is nifty and it’s the very definition of a cult film. Screw the critics.

10. The Spanish Prisoner (1997)

This was a tough choice, as playwright and screenwriter and generally awesome director David Mamet has several heist-themed films to his credit, including the superlative “House of Games,” “Ronin” and, uh, “Heist.” So, there’s that. Those films are slightly better known than this one, which, despite the title, has nothing to do with Spain or a prisoner. Instead, the title refers to an elaborate long con that is too convoluted to get into here, but wholly fascinating. I love stuff like this, and the cast is fantastic, including Campbell Scott, Felicity Huffman, Ben Gazzara, Ricky Jay, Rebecca Pidgeon (Mamet’s real-life wife and frequent star) and a rare dramatic turn from comedy legend Steve Martin. Though not as heist-y as, um, “Heist,” it’s still pretty great. If “Reservoir Dogs” is a heist movie in which we never see the heist, then this is a heist film in which, like the lead character, we’re not sure what the heist even is until late in the game.when the damage has already been done. Now that’s a neat trick.

9. Thief (1981)

Another flick with James Caan, this one is from super-stylish Michael Mann, best known for “Miami Vice” and the epic heist flick “Heat,” which this film is sort of like a smaller-scale version of. The cast is great and includes the debuts of William Peterson (“CSI”), Dennis Farina (“get Shorty”), and James Belushi, as well as the great Tuesday Weld (“Looking for Mr. Goodbar”) and singer Willie Nelson. The memorable synth-driven soundtrack is by pioneering techno band Tangerine Dream, which is worth investing in as well. It’s based on a true story, and is arguably the best-looking film on this list, as per Mann’s usual slick approach. If you liked the recent “Drive,” you should check this out, as it got a lot of its style from the film.

8. The Grifters (1990)

Not unlike #10, this one is all about the so-called “long con,” aka an elaborate plot to dupe some poor sucker- or suckers, as the case may be- into believing something that isn’t true. John Cusack, in a then-breakout dramatic role (he was known mostly for comedies at the time) plays a man who favors more short-term cons, but meets and falls for a fellow con artist that has bigger things in mind, played by Annette Bening at her sexiest. His mom, played by Anjelica Houston (whose father helmed the classic heist drama “The Asphalt Jungle”), who taught him everything he knows, is highly suspicious of this new influence and things only get uglier from there. Based on the classic noir novel by Jim Thompson, produced by Martin Scorsese, with a script by classic noir novelist Donald Westlake, the film was nominated for multiple Oscars, but failed to win and was not a big hit at the box office. It’s definitely worth another look, especially if you’re a fan of any of the above names. Be forewarned Cusack fans: it makes “Grosse Point Blank” look like a feel-good romp.

7. Killing Zoe (1993)

Co-writer of the Oscar-winning screenplay for “Pulp Fiction,” Roger Avary made his directorial debut with this film, about a bank heist gone horribly awry in Paris. Though a few scenes were shot there, the film was mostly shot in LA and was the direct result of a bank location being made available for shooting, intended for “Reservoir Dogs.” (As fans know, the actual heist in that film was never shown, only the aftermath.) Avary knocked out the script in a week and a half and he was off and running, although, ironically, the location wasn’t even used! Nothing like a deadline to get the lead out. And get the lead out Avary does, in this bloody tale of heroin addicts robbing a bank on Bastille Day, also featuring Julie Delpy as the titular Zoe, a prostitute.and bank teller. It’s intense, stylish, and should have led to bigger things for Avary, who also helmed the worth-a-look adaptation of Bret Easton Ellis’ “The Rules of Attraction,” a prequel of sorts to “American Psycho.”

6. Layer Cake (2004)

The directorial debut of Matthew Vaughn, who went on to direct the cult fave “Kick Ass” and the “X-Men” reboot “First Class,” and also produced Guy Ritchie’s early work (see #4 ), this underrated effort was many people’s introduction to Daniel Craig, and was widely considered to be the film which landed him the much-coveted James Bond role. Craig plays a character only known as XXXX who is looking to retire from the drug dealing business. Needless to say, whenever someone wants to “get out of the business” in a crime drama, trouble is bound to ensue, and boy, does it ever. This is gritty, fun stuff, with a sexy, star-making turn from Sienna Miller as a girl Craig takes a shine to. The film is stuffed with beloved Brit character actors and features then-future Bane Tom Hardy in a supporting role, plus an ace soundtrack. If you like Craig as Bond and Vaughn’s other films, especially “Kick Ass,” you’ll love this.

5. Dead Presidents (1995)

Calling this one a mere heist film is doing it an injustice- it’s so much more. In fact, it’s like three films in one: a coming-of-age drama, a Vietnam-era war exploration, and a heist film. The Hughes Brothers follow-up to the critically acclaimed “Menace II Society,” the film received mixed reviews from critics, and wasn’t nearly as well-received as their first film, but it’s worthy of a second look. The soundtrack is one of the best you’ll ever hear, the war scenes are horrific and chilling, and the attention to period detail is phenomenal. The cast is also uniformly excellent, including Larenz Tate, Freddy Rodriguez, Chris Tucker, Keith David, Michael Imperioli, Martin Sheen, Terrence Howard and Bokeem Woodbine (formerly of the rap group Onyx). This is far and away one of my favorite movies of the 90s.

4. Lock, Stock, and Two Smoking Barrels (1998)

The film that put Guy Ritchie on the map, and to me, still his best effort to date- as well as star Jason Statham’s. It revolves around an attempted card game heist that goes horribly awry- mostly because it’s fixed. As the victims scramble to pay the debt they lost, things spiral out of control, getting more and more crazy as they try and get the drop on yet another heist to cover the heist they screwed up- or thought they did- in the first place! After this, Ritchie’s films only got more and more convoluted, including “Snatch” and “Revolver,” and not always in a good way- though I’ll take any of the lot to his lone non-crime themed effort, “Swept Away,” with then-wife Madonna. He did fare better with his eye-popping takes on the ultimate crime solver Sherlock Holmes with Robert Downey, Jr., however. As with most of Ritchie’s films, the soundtrack is top-of-the-line, with a great mix of the known and lesser-known. Though a huge hit in England, it was only a moderate success here in the States, albeit critically-acclaimed across the board. The film is a lot of fun, with footballer Vinnie Jones also making his debut and rocker Sting in a small role, to boot.

3. Miami Blues (1990)

Arguably Alec Baldwin’s best work on the big screen, his brief turn in the superlative “Glengarry Glen Ross” notwithstanding, I never hear anyone talk about this fantastic little movie, another noir-influenced winner. (I owe a huge debt of gratitude to my professor, Dr. Larry Wharton, who introduced me to both this and the novel upon which it was based by Charles Willeford.) Baldwin could not be more bad-assed in this movie. How bad ass? Barely five minutes into the movie, he kills a Hare Krishna in an airport by breaking his finger! Not sure that’s even possible, but it sure is awesome. Later, he steals a cop’s badge and gun and runs around town posing as one and committing crimes! Featuring the underrated Fred Ward, who has a face born for noir- ditto co-star Charles Napier- and an adorable Jennifer Jason-Leigh as a prostitute Baldwin hooks up with. Love, love, love this film. Blu-ray, please!

2. Matchstick Men (2003)

One of those films Nicholas Cage manages to make every now and then when he gets his head out of his own ass, this is a surprisingly touching effort from director Ridley Scott that should have been better received. It’s another con-man tale, but with a neat approach. It revolves around Roy (Cage), who works at conning people with the help of fellow grifter Frank (Sam Rockwell), who he has trained from scratch. Suffering from all manner of issues, he seeks help from a psychiatrist, who encourages him to make peace with his past, including getting to know the daughter he never knew he had, Angela. She’s played by the excellent Alison Lohman (“White Oleander”), who really should be a bigger star by now. Eventually, he confesses his “job” to her and she talks him into teaching her the tricks of his trade, with unexpected results. Based on a novel by Eric Garcia, this is a low-key but effective little noir thriller that has some pretty nifty twists you won’t see coming and excellent performances all around. When people scoff at Cage on the whole, this is the film I recommend they see to change their mind, along with “Wild at Heart.” Sure, he’s pretty nutty here, too, but it’s a good kind of nutty, not the over-the-top insanity he usually pulls. Director Scott also shows remarkable restraint here, making a bona fide character study no one probably predicted he had in him. A truly overlooked gem all around.

1. The Princess and the Warrior (2000)

It isn’t often that heist movies can be called lyrical and poetic, but as with a few select other films on this list, heist film doesn’t quite begin to cover it. Teaming again with actress Franka Potente, director Tom Tykwer- hot off their first-rate collaboration, the critically-acclaimed cult film “Run Lola Run”- this movie is the polar opposite in overall tone, which disappointed some fans of that film. Their loss. This beautiful effort not only rewards multiple viewings, it really stays with you. (It’s also worth mentioning that there are two different versions of the film, with one a slightly more resolved version of a particularly surreal moment in the film. Both are worth a look.) To me, this film alone shows that one can bring a new approach to even the most time-worn of genres, and thus, represents why I did this list in the first place- hence the ranking. I can’t recommend it enough, even if you tend to steer clear of foreign films. (A dubbed version is readily available, so no excuses!) Hope you find some good stuff here, as there’s a little something for everyone on this list. Happy viewing!