In honor Freaky coming out this weekend, we’re gonna rank the Best Ever Vince Vaughn Movies. Let us know @Siftpop what your ranking is!

Have you ever been intimidated by funny-man, Vince Vaughn? You are probably thinking…why? He plays a goof or jerk in all of his films with no ounce of physicality except for a really relaxed demeanor. But have you ever seen him rip a car to pieces with his bare hands? Check out Brawl in Cell Block 99 and it will seriously shock you! S. Craig Zahler brings his old school sensibility and brutality to this crime thriller. Vaughn portrays a brutish former crook who gets blackmailed into going deep into the prison system to save his wife. Vaughn beats plenty of people with his bare hands including ripping a man’s face off by dragging it across concrete. Zahler’s films are brutal and hit like a sledgehammer…but are so hard to turn away from. If you want to take a trip into a John Carpenter-esqe action flick, go no further than Vaughn banger in the form of Brawl in Cell Block 99. (Shane Conto)

Who would love to kick back and watch a good old fashioned, hard-boiled detective drama? Well…S. Craig Zahler has you covered with his epically long and intense cop drama starring the unlikely duo of Mel Gibson and Vince Vaughn. Dragged Across Concrete hits hard and slow with themes of corruption and racial tensions as it gives the audience cops on the edge against driven thieves. Vaughn brings his charm as a sleazy cop who is partnered with a loose cannon and rugged Gibson who has been long passed over for promotion. Neither of these cops play by the rules and Zahler takes the audience on a spiraling descent into their turn to the dark side. Where the film might give up on a driving pace it surely makes up for in a sledgehammer of brutality and challenging morals. They surely don’t make films like this anymore but Zahler, Gibson, and Vaughn deliver the goods. (Shane Conto)

Before he stunned us all with the dramatic masterpiece, Joker, director Todd Phillips made a name for himself by writing and directing low-brow comedies. However, none of those films proved to be as prominent as the 2003 hit, Old School. Led by a trio of unique leading men, (Luke Wilson, Vince Vaughn and Will Ferrell) Old School, tells the story of three, thirty-something year-old friends who try to reinvent themselves by creating their own college fraternity. The movie is very much reminiscent of those rowdy, unashamed 1980’s college-boy movies, such as Revenge Of The Nerds, Porky’s and of course, Animal House. Wilson pretty much plays himself as the level-headed leader Mitch, while Vaughn’s Beanie is just trying to be a good dad and live his best life at the same time. Ferrell loses himself as “Frank The Tank,” a once caged, now unleashed party animal who isn’t against going streaking from time-to-time. Aside from Ron Burgundy, it is one of his most recognizable roles. There are a few plot-holes here and there, but the film does a great job of not taking itself seriously, which is what you’re supposed to do in a frat. And although Old School can be seen as another movie about middle-aged drinking and wild shenanigans, it really is more about understanding that no matter what point you’re at in life, you can always rediscover your purpose and have some fun in the process. (Nick Zambrano)

I first read Into the Wild during my freshman year of college for an Intro to Philosophy class. The reason we read it was to use our newfound terms and ways of thinking to analyze Chris McCandless, the real life subject of the book. At that point, I found the story to be moving, interesting, and thought-provoking, but it wasn’t until I first saw the movie a few months later that it really dawned on me how special the story was. Like the Joker, Chris is sick of the hypocrisy and commercialism of society, but unlike the Joker, he tries to get away from it and just live. Chris misses the beauty immediately in front of his face and tries to escape anyway, and this is displayed eloquently and subtly in a scene with Vince Vaughn’s character (who isn’t doing his typical comedy thing) Wayne Westerberg. The film is a mix of awe-inspiring and sad upon the first watch, but is simply heartbreaking upon the second. It’s well worth your time due to the life lessons alone. (Robert Bouffard)

When it comes to Vince Vaughn later in his career, I think I find myself gravitating more towards his roles that mix that signature Vaughn humor with his more serious acting he has chosen in his later years. This film is a perfect encapsulation of that spirit. To start with, Fighting with My Family was easily one of the most unappreciated films from 2019 and it was also the first of three films that year that showcased the brilliant talent that is Florence Pugh. After her 2019 run, her films are now appointment viewing. While the film is formulaic to an extent, director Stephen Merchant’s comedy chops shine as he details the mostly true story of Saraya “Paige” Knight and her rise into WWE stardom. Vaughn stars as a talent scout as well as early coach and mentor for Knight as she begins her journey and his acerbic sense of humor truly shines. As the movie progresses however, his character ends up providing a lot of the heart and soul of the film. His character has been through the trials and tribulations and Vaughn makes that really clear in an extremely strong performance. All in all, if I can get a chance to discuss one of my favorite movies of 2019, I 100% will. Fighting with My Family is a definite recommendation to anybody who has yet to see it. (Nashua Doll)

Dorthy Mantooth is a Saint! Name a more quotable movie than Anchorman. It might take you a bit and if you pick another movie, I’ll probably respond in the means of some sort of quote from Ron Burgundy. But one of the most impressive feats for this movie is that this isn’t just Will Ferrell’s movie. Christina Applegate, Steve Carell, Paul Rudd, David Koechner, Fred Willard, and so many others (especially everyone in the Anchorman Rumble) are so fun in this movie. And, of course, Vince Vaughn, who perfectly plays a jealous, rival anchorman to juxtapose Ferrell’s Ron Burgundy, and his progression is one of the funniest there is! While Vaughn doesn’t take the leading role in this movie, he is still excellent and this is for sure one of his best roles. (Aaron Schweitzer)

Dodgeball is one of my favorite Vince Vaughn films. It’s one of those films that I’ll watch whenever it appears on TV or just for the laughs. Who thought a film about a game we played in school would be a hit. The film is great because of its crazy antics and screwball comedy, but it worked because of the cast. Vaughn’s performance as the nonchalant owner of Average Joe’s Gymnasium was funny. He wasn’t over the top when it came to whenever Ben Stiller’s White Goodman would show up on the screen. Mr. Vaughn doesn’t have to do such a thing. His delivery was subtle, but quick. I would say he carried the movie on his back, but I would say that’s taking it too far. He did help carry—a little. (Chantal Ashford)

Some of the best War Films take place during America’s Finest Hour, Hacksaw Ridge (2016) is no exception in this regard. This film is based off of real life conscientious objector, medic and war hero, Desmond Doss (Andrew Garfield). Hacksaw Ridge does an excellent job telling it’s story that is backed by powerful and emotional testimonials at the end of the film. It makes you question these amazing feats that Doss is able to accomplish and you can’t help but swell with pride that such an individual existed. This film is overflowing with talent behind and in front of the camera. A standout in this film that is worthy to be gushed over is Vince Vaughn as Sgt. Howell. He has the acting chops to pull off the dramatic moments, but more importantly has the comedic timing to pull off the machine gun like array of insults upon his new recruits. Everytime I watch this film, I can’t wait to see the Boot Camp portion of it due to his banter and hilarious playful, yet degrading remarks he tosses out. Hacksaw Ridge pushes and pulls your emotions in all directions while telling an extraordinary tale of one brave and selfless man. (Joe Vargas)

In terms of rewatchability, this movie is definitely up there. It has a crazy good cast that at the time still had their massive career spikes to come! I’m talking about Bradley Cooper, Rachel McAdams and Isla Fisher. Then of course we have our main pair – Vince Vaugh and Owen Wilson, who’s chemistry is through the roof here, making them absolutely magnetic to watch. Are their characters terrible people? Yes. Do they make some incredibly questionable choices? Yes. Is it surprising that things work out for them, given that most ordinary people would tell them to go away and get a life? Absolutely. However, and most importantly, do you care while you watch this at all? Nope! This is a movie where you definitely forget the moral high ground and just enjoy the quippy humour, fun antics, and deplorable behaviour that happens on screen. So sit back, relax, and let Vaughn and Wilson excite your most base senses. (Alice Micheli)

If you are looking for a hip hangout film that is money, Swingers (1996) is the film for you baby. Starring a young Jon Favreau and Vince Vaughn who are two friends having a great time hanging out. Whether it be Vegas, LA ,or anywhere else in between. Mike (Jon Favreau) is the sensitive type that is going through a difficult break-up that has been dragging down his comedic career and has him in a melancholic stupor. Trent (Vince Vaughn) couldn’t be any different, with a magnetic personality that oozes with confidence. With every word that comes out of his mouth, he is so sure of himself with every bold statement that he makes. Vaughn knows the inner workings of what makes this type of character tick so well and you see a little of himself in the character of Trent. He always has the right thing to say in the particular situation and reads a room like no other. He is the type of guy that men want to be on a superficial level with his quick wit and devil may care attitude. Swingers in itself is a solid cult classic that lives and dies by it’s dynamic characters, LA backdrop, and strong dialogue. (Joe Vargas) 

Honorable Mentions

The Lost World: Jurassic Park

Sometimes, when following up on an instant classic, it’s hard for a sequel to hold a candle to the original.  The Lost World: Jurassic Park does a respectable job at following up the first film of the series, putting up an underrated performance in my personal opinion.  Bringing back mathematician Ian Malcom into the world where dinosaurs are brought back to life, this film this time around the enemy is not the dinosaurs themselves, but the greed of those who want to like their own pockets over the safety of others, as John Hammonds creations are being pursued by his money-driven nephew, while also showcasing how technology has advanced with the use of both practical effects and CGI.  This movie may not be the tour de force the first Jurassic Park was, but solid performances from the likes of Jeff Goldblum, Julianne Moore, Vince Vaugn and Pete Postlethwaite (a name I’m not even going to try to pronounce) makes this sequel enjoyable to watch.  Just know that sometimes, nature should be left to itself. (Joseph Davis)

The Internship

I have a little bit of a weird history with this movie. I remember this movie coming out, thinking it looked totally stupid, hearing it was pretty dumb, and ignoring it. Years later I stumbled across some reviews that surprised me as they were detailing that it actually was a lot of fun. So, I decided to give it a try. I was not disappointed! The Internship stars Owen Wilson and Vince Vaughn, teaming up again 8 years after another movie that appears on this list and the chemistry is just as palpable. You can just tell that these two were meant to be on screen together. Wilson is his goofy, charming self while Vaughn is back to his fast-talking, scheming ways. But there is some serious depth to these characters. Vaughn and Wilson are older now and it is starting to show in how they play their characters. While still a silly comedy, the movie tackles the very really feeling of getting older and feeling left behind by modern day society. Vaughn particularly is showing some serious dramatic depth and it’s actually a nice little sample of the more serious roles he would take in work. Give The Internship a try. It might just surprise you. (Nashua Doll)

Fred Claus

Whenever we typically get a comedy starring Vince Vaughn it’s aimed towards a more adult centered audience, so it’s surprising to see Vaughn do such a film that’s more for the whole family instead. I’m talking about Fred Claus, a movie that most have forgotten as it seems. We’re used to the typical christmas movie that focuses on santa claus, but what I find interesting about this one is that it shows us the story of his lesser known brother named Fred. After years of living in Santa’s (Paul Giamatti) shadow, Fred (Vince Vaughn) makes a deal with his brother to work for him at the north pole for christmas to help him pay off a debt that he owes. I like movies that take something we’ve all seen before with a famous character like Santa Claus and put a new spin on it. They do a fun job at making the origin of Santa and his history with his older brother something new and different for a christmas movie. I’d also like to mention how fun it is to see Giamatti playing as Santa Claus, that alone is something I thought I’d never see and I’m not disappointed with the results. He has the usual charm that we’re used to, but also has that unique spin that Giamatti gives in his performance where we get to see a Santa that feels tired and stressed, which is something we usually don’t see. So since it’s close to that time of year, I’d definitely recommend adding this to your list for next month. (Alex Henderson)

Also see: Couples Retreat, Delivery Man, Domestic Disturbance, Mr. & Mrs. Smith, Rudy, Starsky & Hutch, The Break-Up, The Cell, The Dilemma, Zoolander