Every week at SiftPop.com, we challenge our writers to choose what they think is the best movie under a certain topic related to a recent release. So this week, with the release of The Unbearable Weight of Massive Talent, we’re counting down our favorite movies in which an actor plays themselves! Let us know @SiftPop what your ranking is!
Look, if you haven’t watched this movie yet, I don’t know if we can be friends? Okay, I’ll take it back. But you’re seriously doing yourself a disservice. Popstar: Never Stop Never Stopping is easily one of the funniest movies from the past decade that somehow continues to be underseen. From the geniuses that are The Lonely Island, Popstar is a mockumentary musical comedy that perfectly parodies the real world music industry, expertly toeing the line between complete farce and uncomfortably real. The jokes come a mile a minute, rewarding multiple rewatches as you catch new little details each time. And within the movie, we have one of the most talented comedic casts of the current day. Everyone from Andy Samberg and Jorma Taccone as the leads, to bit parts played by Bill Hader, Justin Timberlake, and Joan Cusack, equally crush it. Additionally, there are a ton of real life people playing themselves. Everyone from Usher and Seal, to Carrie Underwood and Pink, to my personal favorite, Michael Bolton. These cameos never feel silly and all perfectly lend to the overall tone. Bolton’s appearance specifically brings me joy as a longtime Lonely Island fan, and brings his signature powerhouse voice to the incredible climax of the movie. And to cap it all off, the music is perfect. Please go see this if you haven’t. I promise you’ll thank me later. (Nashua Doll)
The Other Guys is a fantastic comedy that is generally lost in the shuffle of excellent Will Ferrell/Adam McKay collaborations. It follows Ferrell and Mark Wahlberg as two New York City cops that are constantly crapped on by members of their own department while other, flashier cops make the headlines. This movie is an example of tremendous absurdist humor with hilarious one-liners that could be quoted for years, and bit parts from the likes of Samuel L. Jackson, Dwayne “The Rock” Johnson, and Michael Keaton that will have your sides splitting. There’s one cameo in particular though that, while short lived, is incredibly relevant to the story, and that’s of one Derek Jeter. Hall of Famer and New York Yankees legend, Jeter played himself in the tragic backstory flashback that shows why Wahlberg’s character is so hated: he shot Jeter in the leg during game seven of the World Series. He cost the city a championship and became known as the Yankee Clipper. How could he shoot Jeter? I mean, he’s a biracial angel. It’s small moments like these that make The Other Guys stand out as a laugh-out-loud riot that stands as a high recommendation for anyone. (Heath Lynch)
If someone said that Bruce Willis was joining the Ocean’s crew for Ocean’s Twelve, that would have been exciting. Well he did indeed get cast! Not for that kind of role though. He was playing… Bruce Willis? Steven Soderbergh goes full meta when the crew needs a “celebrity” for a heist, and pretends that Julia Roberts’ character is, you guessed it, Julia Roberts. But things go sideways in this big set piece when Robert’s friend Bruce Willis crashes their party. This might be one of the strangest meta gags in a film, but it fits right in with the rest of Soderbergh’s arthouse sequel to his box office hit remake. Willis is joined by Vincent Cassel and Albert Finney along with the incredible cast of the first film. It might not be the taste for everyone, but this bold and artful sequel might be one of the most interesting heist films you can experience. (Shane Conto)
Zoolander reveals male models to be at the center of history’s most famous assassinations, with the Malaysian prime minister next on the hit list. The attack is spearheaded by world renowned fashion designer, Jacobim Mugatu (Will Ferrell), who brainwashes male model of the year (for three years running), Derek Zoolander (Ben Stiller), to carry out the hit. When a younger, up-and-coming model, Hansel (Owen Wilson), takes his title in year four, Derek decides that there’s more to life than being really, really, really, ridiculously good looking, and it’s in this moment of despair and realization that he finds himself susceptible to assassination indoctrination. But first, a walk off, with Derek challenging his new number one rival to a competition, which leads to the instantly memorable cameo by the late, great David Bowie playing himself in service as the judge of the proceedings. “Now this’ll be a straight walk off, old school rules: first model walks, second model duplicates, then elaborates. Okay boys, let’s go to work.” In laying out the rules, Bowie lends a gravitas to the scene, punctuated by his astonishment at Hansel’s ability to single-handedly remove his underwear without first removing his pants, and the emphatic disqualification of Derek for not being able to pull off the same feat. Zoolander is wacky fun that doesn’t take itself seriously, while still striving to entertain with intelligently conceived jokes coupled with unapologetic slapstick comedy. (Jonathan Fedee)
Long before he started making Oscar fare like Joker, Todd Phillips was known for his raunchy comedies, most notably, The Hangover. Starring Bradley Cooper, Zach Galifianakis, Ed Helms, a tiger, and Mike Tyson playing himself, among others, this is a wild, hilarious movie about four guys going to Vegas for a bachelor party. Of course, things go very wrong, one of the friends gets lost, and the other guys have to return the tiger they drunkenly stole from Tyson’s house. The cameo shows off that Tyson is definitely tone deaf when it comes to singing, but his role in the movie is hilarious and ridiculous nonetheless. Like any comedy, some of the jokes haven’t aged well, but I still really enjoy The Hangover to this day. (Robert Bouffard)
If you know two basic things about me, it’s probably that I like movies and Boston sports. So while I love movies like Fever Pitch largely because it fits those criteria, there are more objectively better films out there, namely the Safdie brothers’ Uncut Gems. This movie is great — it features a rare dramatic Adam Sandler performance, and he absolutely knocks it out of the park as Howard Ratner, a gambling addict whose pawn shop is visited by none other than Boston Celtics legend Kevin Garnett. KG never acted in a role nearly this size before, and he brings the same energy to a movie set that he brought to a playoff basketball game. He’s the character the whole plot hinges on in this claustrophobic, overstimulating movie about everything coming crashing down at the same time. Uncut Gems is a lot, but it’s a lot of what I love. (Robert Bouffard)
Starring in a musical comedy film during the height of Beatlemania might not be the obvious move for John Lennon, Paul McCartney, George Harrison, and Ringo Starr, but it sure paid off. The influence of the Beatles’ soundtrack for A Hard Day’s Night is clear, but the impact of the film itself can not be overstated. Richard Lester’s work on the musical portions of the film led MTV to declare him “The Father of the Music Video,” and the film’s sense of humor likely inspired comedy films for years to come, This is Spinal Tap being an example which immediately comes to mind. Speaking of humor, John, Paul, George, and Ringo are genuinely hilarious. If some unsuspecting viewer had somehow spent the last 60 years living under the world’s largest rock, there would be no reason to believe that our four leads were anything other than Britain’s latest up-and-coming comedy stars. A Hard Day’s Night is a must-watch for any Beatles fan, though even those largely unfamiliar with the Beatles will find enjoyment in the film’s musical segments and dry, British humor. (Foster Harlfinger)
The more I think about Zombieland,the more I realize how this film was the true definition of “lightning in the bottle.” Think about it — you have Woody Harrelson when he was “coming back” into the spotlight, Emma Stone and Jesse Eisenberg before they became huge, Abigail Breslin in her sweet spot where she has the name recognition, and back in 2009 we were not so sick and tired of zombies as they were not everywhere you look. So the fact you have Bill Murray as himself with (I am calling it right now) the best celebrity cameo of all time, is just a cherry on top of a great cake. I think what differentiates his cameo from any other ones is simple — he genuinely seems to be game for anything in this film. Want to riff? Sure! Want to role play as Ghostbusters? Got it! Want to know what I regret the most? Well… I won’t spoil it for those few who haven’t seen it, but Bill will give it to you straight. I remember watching Zombieland for the first time, not knowing he was in it and how I smiled throughout his entire sequence. This film truly is a once-in-a-lifetime thing, where everything lined up. Don’t believe me? Well, let me just say the 10-years-later sequel, Zombieland: Double Tap,has its moments, but I’ve already forgotten most of it, whereas I still remember quite a few things from the original film and it’s been since 2010 I’ve watched it last. I think it’s time for a rewatch. (Luke Burian)
In 2015, Adam McKay, director of comedy classics like Anchorman and Step Brothers made it onto the scene of prestige cinema with a splash. Based on the book by Michael Lewis, The Big Short explains and portrays the 2007 financial crisis in comedic and captivating fashion. The film is narrated by Ryan Gosling as Jared Vennett, a douchey broker who helps Mark Baum (Steve Carrell) and his team short, or bet against, the housing market. He consistently breaks the fourth wall and allows the audience to understand the jargon of the mortgage crisis with appearances from Margot Robbie in a bubble bath, Anthony Bourdain explaining CDOs with a seafood stew metaphor, and a game of blackjack with Selena Gomez and economist Dr. Richard Thaler. All of these detours really are effective in helping you understand what’s happening in the multiple perspectives of the film, all of which see the imminent crisis coming and want to short the housing market. This film is so well paced and, like all of McKay’s work, is brilliantly edited, incorporating news footage, stock photos, pop culture references and notable quotes to turn a financial biopic into something entirely more fun, interesting, and accessible to truly understand this financial crisis. Also featuring great performances from Christian Bale, Brad Pitt, Tracy Letts, Marisa Tomei, Hamish Linklater, Jeremy Strong, and Melissa Leo, The Big Short holds a spot as one of the best films of the 2010s. (Jacob Kinman)
When I was in college, a group of friends wanted to watch a movie. We went to our local Family Video (remember those?) and nothing was standing out. Someone finally picked up Being John Malkovich and we all had a vote on who wanted to watch it. The biggest detractors were people who thought, “why on Earth would anyone want to watch a movie about Cyrus ‘The Virus’ Grissom?” I was the tie breaker vote and voted yes because I was curious. I had heard great things, but wasn’t prepared for how wonderfully weird this was. I loved the performances and give credit to Malkovich for doing some great work and deep down being a good sport about this. The effects were pretty cool, and this was such an original idea that I couldn’t keep my eyes off it. I was the only one who liked the movie, and still to this day one of those friends brings up how I ruined the night by picking Being John Malkovich. Worth it though. (Mike Hilty)
Captain Marvel
Let’s be honest… we all got a little emotional when Stan Lee smiled up at Carol Danvers in Captain Marvel, his first posthumous Marvel appearance, released three months after his passing. In that same film, we got a Lee-themed opening intro, one of many tributes included to the man that without whom, the Marvel Cinematic Universe (and most other iconic pieces of comic book culture) would not exist. From his first cameo appearance in Iron Man, in which Tony Stark mistakes him for Hugh Hefner, it was clear that Lee’s presence would be important to every subsequent film, even though they were only cameos — whenever he popped up, it was something that everyone (even casual fans) could recognize. In fact, his Captain Marvel appearance is one of his simpler ones, done with barely any dialogue, but because of the previously-unintentional weight it carries, it is one of his most effective. And with a Mallrats script in hand, this is one of the clearer instances of Lee playing himself. There isn’t a movie fan out there that can deny Lee’s ineffable contribution to modern pop culture. Even though he lived a long and fruitful life, it still feels like Stan Lee was gone too soon, and whenever I rewatch a Marvel film, Captain Marvel included, my face always lights up when he crosses the screen. (Rowan Wood)
Man on the Moon
Andy Kaufman is a certifiable genius, and one of the greatest pioneers of anti-humor and shocking nihilism in the history of entertainment. He was also taken way too soon, passing away at the incredibly young age of 35 due to cancer. If awkward and intentionally uncomfortable humor is not your style, then Kaufman is not your man. But if you want to learn more you have to check out Man on the Moon, an amazing biopic starring Jim Carrey as Kaufman giving one of the best performances of his career right up there with The Truman Show and Eternal Sunshine of the Spotless Mind. It’s also directed by the legendary Milos Foreman, a two time Oscar-winner for directing One Flew Over the Cuckoo’s Nest and Amadeus. This movie is also littered with tons of cameos by performers that Kaufman worked with throughout his career playing themselves. You have the major players from the late ‘70s to early ‘80s sitcom classic, Taxi, including spots from Judd Hirsch, Carol Kane, Christopher Lloyd, and Jeff Conaway. The movie also takes a look at Kaufman’s wrestling career as a heel starring an elaborate prank storyline with Jerry Lawler. That also includes a spot with wrestling announcer Jim Ross, and a re-creation of a stunt with David Letterman on his Late Night show. Biopics can sometimes be played out, but Man on the Moon offers a look into the world of a truly unique talent. It’s both hilarious and moving, and is a definite recommendation. (Heath Lynch)
Dodgeball: A True Underdog Story
Every so often a comedy comes along that defines an era, and in 2004 that movie was Dodgeball: A True Underdog Story. The movie is about Peter La Fleur (Vince Vaughn), who needs $50,000 to save his gym, so his ragtag group of friends who are also employees and customers join a dodgeball league to win the money. As with all great sports movies, there is a rival, White Goodman (Ben Stiller), who wants to cause Peter’s team to lose so he can own his gym. There are tons of recognizable people who show up in this film including Christine Taylor, Justin Long, Stephen Root, Rip Torn, Alan Tudyk, and Jason Bateman. Lance Armstrong even shows up to motivate Peter to do the right thing in finishing what he started. Like all great sports movies, they need a panel of judges, and of course have a celebrity judge — here, they bring none other than Chuck Norris. When this movie came out, everyone was quoting the lines, and I still quote them today. This is a great movie that seems to have been forgotten to time. “If you can dodge a wrench you can dodge a ball.” (Austen Terry)
Fighting With My Family
I describe the 2019 movie year as Florence Pugh’s year, as she had three hits, with the first being Fighting with My Family. This movie tells the story of WWE star Saraya (Pugh), whose brother Zak (Jack Lowden), and parents Ricky (Nick Frost) and Julia (Lena Headey) love pro wrestling — one day, Zak and Saraya get the chance to audition for the WWE. Having a movie based in the realm of Pro Wrestling, you need to have a charismatic star to come along to help Saraya on her journey, and who better than Dwayne “The Rock” Johnson? He is here more than just a cameo — The Rock shows up multiple times and has some great scenes with Zak and Saraya. This film will take you to the mat with its humor and heartfelt story as you go on Saraya’s journey. Pugh is phenomenal here and really shows why she is quickly becoming a beloved star. This film has flown under the radar for a lot of people, and if you haven’t seen it, I highly recommend watching it. (Austen Terry)
Always Be My Maybe
Always Be My Maybe is an excellent modern romantic comedy that revolves around the blending of two worlds. Ali Wong plays Sasha, the ambitious celebrity chef that is making waves in the culinary scene, and Randall Park plays Marcus, the love interest and foil of Wong’s character. Marcus is afraid of change. He’d rather continue to play small venues with his band than aspire to something greater and leave his hometown of San Francisco. One of the characters that works to embody Marcus’ aversion to fame and success is Keanu Reeves, appearing as a caricature of himself. Keanu is absurd, theatrical, and pompous. Although his character shares his name, I believe he is designed to be more of a satire of his peers than himself. The film expertly uses one of Hollywood’s most beloved faces to mock the arrogant nature of rich culture. Keanu’s playful, self-aware performance leads to some of the most memorable scenes in the film. It also affirms that he is one of the most genuine and grounded stars working today. (Jack Grimme)
Harold and Kumar Go to White Castle
Back in 2004, when Harold and Kumar Go to White Castle released, Neil Patrick Harris had faded from the public eye and aside from the random TV episode or some DC Animation voice work, was known to most as the kid from Doogie Howser, MD. He was still a year away from co-starring in How I Met Your Mother and it would be two more years before he came out as gay. So when he showed up in Harold and Kumar as a womanizing booze fiend and drug hound, it was not only shocking, it was downright hilarious! The scene where he is sticking out of the sunroof with two topless women, doing lines off one of their butts as the car drives by at excessive speed is the ultimate example of a wholesome child star going wild. Who knew that little Doogie Howser could be so irreverent and hilarious in the process? This movie gave Harris’ career the jumpstart it needed and brought him back into our lives for the better. He went on to be in a long-running, hilarious sitcom, has had many more live action and animated movie appearances, including the sequels to Harold and Kumar, and has written several acclaimed children’s books of which my daughter is a huge fan. Harris has given us so much since 2004, and I believe it’s all thanks to the cameo as “himself” in Harold and Kumar Go to White Castle. (Nick Ferro)
This is the End
The Evan Goldberg/Seth Rogen partnership is among the most influential when it comes to the comedic forces in the 21st century. When you then get all their frequent collaborators, like James Franco and Jonah Hill, together to play heightened versions of themselves in an absurdist end of-the-world scenario, This is the End, it makes for a fun watch. The chemistry between the crew allows for a lot of creative freedom and some great ad-libbed moments. The insanity that was apparently the set really comes through on screen and adds to the tone. Top it off with some great cameos from Michael Cera, Channing Tatum, and Emma Watson, and you’ve got the makings of another fun, raunchy comedy. (Jake Bourgeois)
Trainwreck
It’s time we all acknowledged the truth: LeBron James is better than Michael Jordan… at acting. Debate this. Discuss that. Go about the conversation however you would like. But one can’t ignore King James’ acting chops that were on display in Trainwreck. His comedic timing and line readings are both great. His willingness to not take himself seriously makes his scenes flow well. When he is on camera with seasoned performers like Bill Hader and Amy Schumer, he holds his own. Could MJ do that? No. He was getting circles acted around him by Bugs Bunny. I rest my case for the GOAT debate. (Samuel Nichols)
Jay and Silent Bob Strike Back
So it’s probably a bad time for me to mention this, but I’ve never seen a Kevin Smith film before this one. Though, while I wait for the people to tell me how I’m missing out on his films, I figured I’d at least talk about Jay and Silent Bob Strike Back. I’ll be honest, the fact I hadn’t seen a Kevin Smith joint before put me at a disadvantage, because while I did find this movie fun, I feel like seeing his earlier films would have made this one even more fun. I like the camerawork presented here, the story is fun if not absurd, you have in my opinion one of the funniest fourth wall breaks in film history, and my god, the amount of people in this movie. Obviously you have the current day mainstays of Ben Affleck and Matt Damon, but to also have the likes of George Carlin in what is essentially a bit role is profoundly absurd to me. I’m going to have to revisit this one after watching the rest of the View Askewniverse leading up to it, but Jay and Silent Bob Strike Back is one I’ll gladly pick up again one day. (Joseph Davis)
Space Jam
When I think about Space Jam, I see Michael Jordan and Bugs Bunny flash across the screen before the booming bass of the theme, “Space Jam,” comes through the speakers. It’s true nostalgia, especially since it was the first (and last) time we see Jordan on the big screen. With Looney Tunes characters being in danger, Bugs Bunny enlists the NBA star to help the characters in a basketball game against aliens to keep them from becoming unwilling attractions at an amusement park. In a film all about the game of basketball, you have to have the right star — the one who has the star power. Who better than Air Jordan? He was guaranteed to get the kids in those seats to see their favorite legend along with their favorite cartoon character. With no acting roles in his resume, Jordan does pretty well since he had people in green suits as his acting partners. For a film in 1995, the animation and live action mix was outstanding. Space Jam is one of those features that defined my childhood, with the crazy antics from the Tunes, the wildest game on screen between the Tune Squad and the Monstars, and the several appearances from our favorite NBA players. It’s one of those feel-good movies that take you down memory lane. WB tried to catch the magic again with Space Jam: A New Legacy with LeBron James. Let’s just say it came a little too late. (Chantal Ashford)
I’m Still Here
I’m Still Here is an intriguing dive into celebrity culture and how we differentiate what is reality from fiction. Joaquin Phoenix dives deep into a facet of himself who is leaving acting to pursue a career as a rapper. He is very convincing in the idea that this is an actual career path, and it is very difficult at times throughout the film to tell if he is serious. It is entertaining to see people’s reactions to Phoenix’s actions and words, especially those who are in the music industry like Sean “Puffy” Combs. The disheveled appearance that he takes adds to the believability that he may have lost his mind. If you are into experimental filmmaking and something outside of the norm, I’m Still Here will scratch that itch. (Joe Vargas)
Last Action Hero
We often talk about movies that either could not get made anymore, because some sort of thought behind filmmaking has gotten lost, or people just don’t want to see the same kinds of movies these days. Across from that are the movies that we say were ahead of their time — movies that had ideas they could play with that maybe would have found a better reception if they were released later. Last Action Hero appears right at the crossroads of these two lines of thought. It’s so incredibly meta about action movies of the ‘80s and ’90s in a way that you expect Ryan Reynolds to quip about these days, but it is also one of those action movies itself. It relishes in the absurdity of its own premise to the point where Arnold Schwarzenegger attends the premiere of his own new Jack Slater movie while Jack Slater the character tries to prevent his actor’s assassination. It is such a film of its era that it’s hard to imagine it would be made today, but movies these days do fit its mood a lot more closely than its contemporaries did. Last Action Hero is a strange beast, but it might also be one of Arnold’s best action movies for the simple fact that he does get to make fun of himself. (Chris Bakker)
Ted 2
There are a few hills I am willing to die on — sweet snacks are better than salty snacks, Saoirse Ronan should have had at least one Oscar by now, and Seth MacFarlane is a generational talent who can do it all. And Ted 2 is unfairly seen as the “worse” one. I think the reason people didn’t like it as much was because the novelty factor (a teddy bear who likes to swear, drink, and does many other “adult things”) had worn off, and people were looking for something more. I thought Seth delivered by making this film more about what constitutes being a human. And having re-watched it not that long ago, I thought the movie still held up better than people give it credit for. It’s partly due to a great addition of Amanda Seyfried (talk about another underrated actress, by the way) and the cameo by Liam Neeson. He only has two scenes, one in the first half of this film and one right after the credits, but his cameo is so brilliantly weird and disturbing, you will remember it. I would 100% recommend giving Ted 2 another chance if it’s been a while since you last saw it. You might be surprised how funny and poignant this film is. (Luke Burian)