A ranking of the 50 best comedy movies on Amazon Prime Video, including Happy Gilmore, American Ultra, The First Wives Club and much more hilarious favorites.
They say America’s favorite pastime is baseball, but we all know it’s really going to the movies. Whether it’s a gritty drama, an action tentpole, an animated adventure, or a laugh-out-loud romantic comedy, escaping into a good movie is a hobby everyone has in common. Of course, our choice of concessions may vary.
Well, Amazon Prime Video provides the joys of a theatre-going experience without having to leave the comfort of your couch. From old favorites to recent releases, the streaming giant serves up offerings for film fans of every genre.
When it comes to comedies, Amazon’s queues are stocked up with quotable classics like Legally Blonde and Austin Powers, heartwarming dramedies like The Truman Show and Miss You Already, and newer blockbusters like The Switch and Hot Pursuit. Each of these hilarious films is begging to be the subjects of your next movie night.
We all need a burst of good humor to escape the chaos of everyday life. Thankfully, Amazon Prime Video features some comedic cinematic escapism for everyone. Find your next movie marathon in our comprehensive list of the 25 Best Comedy Movies on Amazon Prime Video.
Updated: March 3
25. Dirty Grandpa
Release Year: 2016
Written By: John Phillips
Directed By: Dan Mazer
Starring: Robert De Niro, Zac Efron, Zoey Deutch, Aubrey Plaza, Dermot Mulroney, Jason Mantzoukas, Julianne Hough
Robert De Niro plays the grandpa to Zac Efron in this raunchy that was directed by the producer of Borat, Bruno and Da Ali G Show. When De Niro’s wife passes away, he comes up with a plan to trick his grandson into going on a spring break trip with him so he can relive his youth. He was a little devious but he says his wife’s dying wish was for him to have fun and his idea of having fun is to get laid by a younger lady.
So enter the spring break madness and debauchery. Efron’s character was all set to get married but now he has to drive to spring break where his grandpa is a terrible influence and where Zoey Deutch and Aubrey Plaza’s characters help bring out the party animal inside them.
24. Happy Gilmore
Release Year: 1996
Written By: Dennis Dugan
Directed By: Tim Herlihy and Adam Sandler
Starring: Adam Sandler, Christopher McDonald, Julie Bowen, Carl Weathers
In the one-two punch of Adam Sandler’s star-making roles, 1995’s Billy Madison and 1996’s Happy Gilmore set Sandler up to become a household name and bankable (albeit critically panned) box office superstar. Billy Madison placed the tee, and Happy Gilmore quite literally drove the hole-in-one home.
Happy Gilmore tells the wild story of an aggressive and failed aspiring hockey player discovering an unprecedented talent for the game of golf. Happy (Sandler) weathers his temper on the links while competing against a fierce opponent, Shooter McGavin (Christopher McDonald), on the Pro Golf Tour. Can he calm his ice hockey instincts and harness his golfing zen?
Chances are, you have already seen Happy Gilmore and belly laughed along with his outbursts. Tap into nostalgia with the classic favorite that precedes other Sandler staples The Wedding Singer and Big Daddy. Without a doubt, you’ll be quoting most every line for the next month.
23. The Addams Family
Release Year: 1991
Written By: Caroline Thompson and Larry Wilson
Directed By: Barry Sonnenfeld
Starring: Anjelica Houston, Raul Julia, Christopher Lloyd, Christina Ricci, Jimmy Workman
Perhaps one of the most ubiquitous and frightening families in pop culture, the Addams Family came to life on the big screen in 1991 after a string of cartoons and sitcoms. Finally, we saw Morticia, Gomez, Uncle Fester, Wednesday, and the whole creepy crew in all their glory.
In The Addams Family, the most successful iteration of the dark fantasy comedy to date, Gomez (Raul Julia) and Morticia Addams (Anjelica Houston) concoct a scheme to wake the dead as a morbid welcome wagon for who they think is Uncle Fester (Christopher Lloyd) after his 25-year disappearance in the Bermuda Triangle.
The Addams Family’s excellent cast breathes new life into familiar and iconic characters in the first film and its sequel, Addams Family Values, which is also available to stream on Amazon Prime Video. If you’re a fan of campy supernatural comedies, the mysterious, spooky, and altogether ooky The Addams Family is the movie for you.
22. Be Cool
Release Year: 2005
Written By: Peter Steinfeld
Directed By: F. Gary Gray
Starring: John Travolta, Uma Thurman, Vince Vaughn, Cedric the Entertainer, Andre Benjamin, Stephen Tyler, Christina Milian, Harvey Keitel, The Rock, Danny DeVito
Among this list, there are handfuls of really great ensemble casts. But are any of them as stacked and star-studded as this one? Be Cool, the sequel to the 1995 hit film Get Shorty (both of which are based on novels by Elmore Leonard), finds the crime story set in a completely different world.
While Get Shorty (which can also be streamed for free on Amazon Prime Video) follows the unraveling of a crime in the film industry, Be Cool sees the gangsters turn into music moguls as Chili Palmer (John Travolta) revives a record company for his friend’s widow, Edie (Uma Thurman). The plot twists turns and spins crazily round and round like a record.
Directed by F. Gary Gray (Friday, The Italian Job, Straight Outta Compton), Be Cool features a wild and thrilling story backed up by a who’s who of a cast. Make it a back-to-back crime comedy double feature with Get Shorty and Be Cool on Amazon Prime Video!
21. Major League
Release Year: 1989
Written By: David S. Ward
Directed By: David S. Ward
Starring: Tom Berenger, Charlie Sheen, Corbin Bernsen, Margaret Whitton, James Gammon, Rene Russo, Bob Uecker
Of course, the comedy film genre wouldn’t be what it is without the sports comedy sub-genre. Think of all of the movies about the world of sports that have become instant classic mainstream hits: A League of Their Own, Cool Runnings, Bend It Like Beckham, and pretty much every Will Ferrell movie from the ’00s.
But one of the enduring favorites, Major League, proved the successful marriage of America’s two most popular pastimes: Watching movies and playing baseball. Unlike most sports comedies, Major League takes place, well, in the major league. But like most sports comedies, the film tells the stories of washed up underdogs rising through the ranks to prove their new owner wrong.
Written and directed by David S. Ward, writer of The Sting and Sleepless in Seattle, Major League features an excellent cast of Tom Berenger, Corbin Bernsen, and in-his-prime Charlie Sheen. The film spawned two sequels, but neither of them could match the home run of Major League.
20. Seven Psychopaths
Release Year: 2012
Written By: Martin McDonagh
Directed By: Martin McDonagh
Starring: Colin Farrell, Sam Rockwell, Woody Harrelson, Christopher Walken, Tom Waits, Abbie Cornish, Olga Kurylenko
Unless you have your ears pressed to the independent film scene, you probably haven’t heard about Seven Psychopaths. However, you certainly have heard about and watched the talents of its ensemble cast many times throughout your movie watching career.
Starring Colin Farrell, Sam Rockwell, Woody Harrelson, Christopher Walken, and Abbie Cornish, Seven Psychopaths leans more into black comedy territory and dabbles in meta-storytelling. In short, Martin McDonagh’s follow-up to his acclaimed black comedy In Bruges isn’t the light and mindless romp of the preceding film on this list.
When his ragtag group of friends swipes a crime boss’ prized dog, a starving artist screenwriter (Farrell) finds himself caught in the mix of the underground world of Los Angeles crime that he’s only written about. Seven Psychopaths pulls you in with a compelling premise and keeps your attention with smart dialogue and a bit of bloody humor. Don’t miss it!
19. Barely Lethal
Release Year: 2015
Written By: John D’Arco
Directed By: Kyle Newman
Starring: Hailee Steinfeld, Sophie Turner, Jessica Alba, Samuel L. Jackson
Hailee Steinfeld made quite the entrance in Hollywood at the age of 14. She landed her first Academy Award nomination for her star-making turn in the Coen brothers’ True Grit. Just six years later, Steinfeld has racked up an admirable résumé, which includes Pitch Perfect 2, hit pop songs (you’ve probably heard her on the radio), and her most recent Golden Globe-nominated performance in The Edge of Seventeen.
Barely Lethal, another starring role for the Hollywood triple threat, follows the exploits of a teenage special ops agent (Steinfeld) who has only ever dreamed of living an average adolescent life. After being assigned to catch an arms dealer (Jessica Alba) by her trainer (Samuel L. Jackson), Agent 83 fakes her death in order to assume the identity of an “exchange student” and experience the majesty of run-of-the-mill teen life.
Directed by Kyle Newman, the action film, and teen comedy hybrid features a knockout supporting cast including Jessica Alba, Samuel L. Jackson, Thomas Mann, Sophie Turner, and Hairspray Live! standout Dove Cameron. With humor, thrilling action sequences, and a compelling lead in Hailee Steinfeld, you’ll want to shoot Barely Lethal straight to the top of your watch list.
18. Fletch
Release Year: 1985
Written By: Andrew Bergman
Directed By: Michael Ritchie
Starring: Chevy Chase, Joe Don Baker, Dana Wheeler-Nicholson, Richard Libertini, Geena Davis, Kareem Abdul-Jabbar, Tim Matheson
In case you weren’t aware, Chevy Chase was a bankable fixture on the big screen in the late ’70s and the 1980s with monster hits like Foul Play, Caddyshack, National Lampoon’s Vacation (and European Vacation), Spies Like Us, and Three Amigos. Got all that?
In 1985, Chase starred in his latest comedy sensation Fletch as a shape-shifting newspaper reporter. To attain the detail to the biggest stories, Fletch does whatever it takes. But when he’s bribed to murder a millionaire, Fletch digs deeper into the truth and it nearly costs him his life.
Fletch preceded the well-received sequel (spoiler alert) Fletch Lives, which finds the investigative reporter in even more turmoil and dangerous situations. If you’re a fan of throwback comedies, Chevy Chase, or even a combination of the two, Fletch is the perfect movie night pick for you.
17. Austin Powers: The Spy Who Shagged Me
Release Year: 1999
Written By: Mike Myers and Michael McCullers
Directed By: Jay Roach
Starring: Mike Myers, Heather Graham, Michael York, Robert Wagner, Seth Green, Mindy Sterling, Rob Lowe, Elizabeth Hurley
Who doesn’t know and most likely love the comedy stylings of one international man of mystery Austin Powers? If you grew up in the ’90s or were a product of Gen X, you came of age in the midst of the height of the Austin Powers franchise’s popularity.
In 1997, Austin Powers: International Man of Mystery introduced the world to the crazy title character and his hilariously high-stakes career. But in Austin Powers: The Spy Who Shagged Me, the sequel to the first blockbuster, the bumbling spy once again faces off against Dr. Evil. Using a time machine, Dr. Evil travels back in time to 1969 to steal Austin Powers’ mojo. From there, it’s a wild back and forth of outlandish high jinks.
Few films can transport the viewer to a moment in time, but Austin Powers: The Spy Who Shagged Me can do just that. Whether it’s to the wild Austin Powers parody of the 1960s or simply to the late 90s soundtracked to “Beautiful Stranger” by Madonna, the Mike Myers-led laugh-out-loud comedy throws you right back.
16. Hot Pursuit
Release Year: 2015
Written By: David Feeney and John Quaintance
Directed By: Anne Fletcher
Starring: Reese Witherspoon, Sofia Vergara
The first of two films on this list starring Reese Witherspoon, Hot Pursuit stars the Academy Award-winner alongside Sofia Vergara, the Emmy-nominated Modern Family actress. Witherspoon produced the buddy comedy under her Pacific Standard banner in her crusade to bring better roles for women into Hollywood, as she did with Wild and Gone Girl.
Hot Pursuit hits the road with an overeager police officer (Witherspoon) and the wife of a drug kingpin (Vergara) as they stay off the path of a pair of crooked cops. While on the run, Cooper and Riva bump into trouble at every turn from Cooper’s accidental cocaine high to a deadly quinceañera.
After a short run of taking on more serious roles, Hot Pursuit marked Reese Witherspoon’s return to playing comedic characters. In her early work, Witherspoon crafted truly memorable comedic characters with Election’s Tracy Flick, Legally Blonde’s Elle Woods, and Sweet Home Alabama’s Melanie “Felony Melanie” Smooter. And with Vergara by her side, they are an unstoppable dynamic duo.
15. Barbershop
Release Year: 2002
Written By: Mark Brown, Don D. Schott, Marshall Todd
Directed By: Tim Story
Starring: Ice Cube, Anthony Anderson, Sean Patrick Thomas, Eve, Michael Ealy, Troy Garity, Keith David, DeRay Davis, Cedric the Entertainer
Kicking off a franchise of films set in a barbershop in the South Side of Chicago, 2002’s Barbershop opened the doors to the fictional business as well as the hilarious hit films. The comedy comes from director Tim Story, who also directed such blockbusters as Fantastic Four, Think Like A Man, and the Ride Along series.
After Calvin (Ice Cube) inherits his deceased father’s middling barbershop, he chooses to wash his hands clean of the business. However, after selling it to the greedy Lester Wallace (Keith David), Calvin attempts to get his inherited barbershop, an important community establishment, back from the conniving loan shark.
Barbershop tells a story larger than a crazy day in an average salon. The film highlights the themes of community and family, while also obviously delivering big laughs. Boasting an impressive ensemble cast, the 2002 film launched a number of sequels from Barbershop 2, Beauty Shop, and 2016’s Barbershop: The Next Cut. See where the laughs began on Amazon Prime Video!
14. Notting Hill
Release Year: 1999
Written By: Richard Curtis
Directed By: Roger Michell
Starring: Julia Roberts, Hugh Grant
Remember all those years ago when romantic comedies were enormously hot properties that broke the box office and our hearts in one fell swoop? Unfortunately for those of us who love the genre, those days are over. Romantic comedies rarely arrive anymore with a bang but instead a fizzle. However, when romcoms were still a booming business, Julia Roberts was the CEO.
Starring opposite rom-com legend Hugh Grant, Roberts’ Notting Hill tells a tale of love as old as time. Following a meet-cute in Will’s (Grant) independent bookstore, he and American celebrity Anna Scott (Roberts) begin a whirlwind romance in the London neighborhood of Notting Hill. As you could imagine, it follows the familiar beats of a romantic comedy but is completely charming and original in its own right.
Notting Hill initially set the record for a romantic comedy film’s opening weekend gross at the box office (later beat by Roberts’ own Runaway Bride) and went on to dominate throughout its run. Without a doubt, Notting Hill left its mark on the romcom landscape and is a definite must-watch whether you’ve never seen it or can recite its script line for line.
13. American Ultra
Release Year: 2015
Written By: Max Landis
Directed By: Nima Nourizadeh
Starring: Jesse Eisenberg, Kristen Stewart, Topher Grace, Connie Britton, Walton Goggins, John Leguizamo, Bill Pullman, Tony Hale
Without even realizing it, Jesse Eisenberg and Kristen Stewart have a lot in common with Emma Stone and Ryan Gosling. They are both massively successful Hollywood actors, they star in movies that leave us obsessed, and they happen to do these things well together. American Ultra becomes the latest film the pair star in opposite each other after Adventureland and Café Society.
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Proving that some things are better together, like macaroni and cheese and the aforementioned Emma Stone and Ryan Gosling, Jesse Eisenberg and Kristen Stewart shine in American Ultra. Eisenberg stars as Mark, a stoner who unknowingly becomes a target CIA sleeper agent along with his longtime girlfriend Phoebe (Stewart).
The action comedy twists and turns and throws out laugh after laugh. Eisenberg and Stewart are backed by an excellent supporting cast in Connie Britton, Topher Grace, Walton Goggins, Tony Hale, and Lohn Leguizamo. If you’re looking for an explosive comedy, American Ultra will deliver the thrills.
12. The Truman Show
Release Year: 1998
Written By: Andrew Niccol
Directed By: Peter Weir
Starring: Jim Carrey, Laura Linney, Noah Emmerich, Natascha McElhone, Holland Taylor, Ed Harris
What if your life was a reality show broadcast nationwide for millions to watch? What if you didn’t know your life was a reality show and everyone around you was playing a part? Well, thankfully, reality television shows don’t really work that way. However, for Truman Burbank, he’s grown up as the subject of a television simulation.
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The Truman Show follows the real but manipulated life of Truman (Jim Carrey) as Hollywood executives have kept him confined on a film set for his entire life. Christof (Ed Harris) controls and broadcasts every aspect of Truman’s life, such as his “wife” Meryl (Laura Linney). Adopted and raised by a corporation, Truman begins to notice inconsistencies in his surroundings and realizes the truth.
Known for his bombastic comedic roles in films like Ace Ventura and Dumb and Dumber, The Truman Show marked Jim Carrey’s conscious but slight departure into more dramatic fare. While still funny (come on, it’s Jim Carrey!), the film explored deeper themes and earned Carrey a Golden Globe for drama acting. The Truman Show is must-see TV and a must-watch movie.
11. Ocean’s Eleven
Release Year: 2001
Written By: Ted Griffin
Directed By: Steven Soderbergh
Starring: George Clooney, Matt Damon, Don Cheadle, Bernie Mac, Scott Caan, Casey Affleck, Elliott Gould, Andy Garcia, Brad Pitt, Julia Roberts
Lighting the match that ignited one of Hollywood’s most exciting big-screen trilogies, Steven Soderbergh’s Ocean’s Eleven remake burst onto the scene with a sizable gross and rave reviews. Surely, we have all seen each of the films, if not have heard about them enough to feel like we were a part of Danny Ocean’s team.
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After he’s sprung from the slammer, Danny Ocean (George Clooney) throws together a crew of capers and con artists to pull off a hefty heist in Las Vegas. The cast also includes megawatt movie stars Brad Pitt, Julia Roberts, Matt Damon, and Don Cheadle among a whole heap of recognizable co-stars.
Ocean’s Eleven brought a welcome dose of comedy to the heist genre and defined the early 2000s with its all-star cast. And now is definitely a good time to give the original Ocean’s trilogy a rewatch. In summer 2018, Ocean’s 8 and its cast of badass women (Cate Blanchett, Sandra Bullock, and Anne Hathaway to name a few) will take the reins from Danny’s squad.
10. Morris From America
Release Year: 2016
Written By: Chad Hartigan
Directed By: Chad Hartigan
Starring: Craig Robertson, Markees Christmas, Carla Juri, Lina Keller, Jakub Gierszal
In a Cinderella story out of 2016’s Sundance Film Festival, Craig Robinson-starrer Morris From America became the little movie that could, defying odds and winning over critics and audiences alike. Another dramedy, the coming-of-age film explores what happens when a father and son move to Germany.
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After the passing of his wife, Curtis (Robinson) relocates himself and his son Morris a.k.a. “Mo” (Markees Christmas) across the pond to Germany, where Curtis coaches soccer and Morris tries to fit in. When you’re a hip-hop obsessed teenager from American learning to live in another country, coming of age doesn’t come easily.
Craig Robinson, a comedy favorite known for NBC’s The Office and big screen hits such as Pineapple Express and Hot Tub Time Machine, anchors the film in a Sundance Special Jury Prize-winning performance. Along with Markees Christmas’ breakout role and Chad Hartigan’s touching script, Morris From America definitely ranks as one of the best comedies on Amazon Prime Video.
9. Up in the Air
Release Year: 2009
Written By: Jason Reitman and Sheldon Turner
Directed By: Jason Reitman
Starring: George Clooney, Vera Farmiga, Anna Kendrick, Danny McBride
Much like other films featured on this list, Up in the Air isn’t a laugh-out-loud hilarious comedy like most moviegoers are accustomed to. But the second entry in director Jason Reitman’s unbeatable trio of bitingly funny films about flawed characters is as light and airy as it title suggests.
Just as Juno’s Juno MacGuff unpacks the implications of young love and teenage pregnancy and Young Adult’s Mavis Gary navigates the murky waters of the post-high school plummet, Up in the Air’s Ryan Bingham (George Clooney) searches for stability. Although his frequent flyer miles and unattached attitude suggest differently, Ryan meets two women, Natalie (Anna Kendrick) and Alex (Vera Farmiga), who alter his flight path.
Up in the Air became a critical darling, earning six Academy Award nominations—including Best Picture, Best Director, Best Adapted Screenplay, Best Actor, and individual Best Supporting Actress nods for Vera Farmiga and Anna Kendrick. For a poignant yet playful look into the lens of the executive world, Up in the Air is just the ticket.
8. Miss You Already
Release Year: 2015
Written By: Morwenna Banks
Directed By: Catherine Hardwicke
Starring: Toni Collette, Drew Barrymore, Dominic Cooper, Paddy Considine, Tyson Ritter, Frances de la Tour, Jacqueline Bisset
Has anyone ever shone brighter onscreen than Drew Barrymore? And paired with the powerhouse performer and insanely likable Toni Collette, the enviably talented duo radiate through laughter and tears in the heartbreakingly funny dramedy Miss You Already.
Milly (Collette) and Jess (Barrymore) have been best friends forever. When Milly’s diagnosed with breast cancer and Jess becomes pregnant, the inseparable pair must lean on each other more than ever to make it through the tough times. While not entirely a comedy, at least not in the traditional sense, Barrymore and Collette bring levity to the heavy, realistic drama.
Directed by Twilight and Thirteen director Catherine Hardwicke, Miss You Already breathes fresh air into the tearjerker genre as the health crisis focuses on the foundation of a friendship rather than a relationship. And with Drew Barrymore taking a break from the big screen, we need to savor every cinematic moment we can get from her. We miss her already.
7. The Switch
Release Year: 2010
Written By: Allan Loeb
Directed By: Josh Gordon and Will Speck
Starring: Jennifer Aniston, Jason Bateman, Patrick Wilson, Juliette Lewis, Jeff Goldblum
We’ve seen them star together in Horrible Bosses, its horrible sequel, and most recently Office Christmas Party. But comedy favorites Jennifer Aniston and Jason Bateman kicked off their string of co-starring roles with 2010’s heartfelt and quietly successful The Switch.
Originally titled The Baster, The Switch finds Aniston’s Kassie living life to the fullest and having a child via artificial insemination. However, during a drunken fit of jealousy, Wally (Bateman) inadvertently swaps Roland’s (Patrick Wilson) sperm sample for his own. Seven years later, Kassie returns to New York City and Wally realizes what he has done.
Simply, The Switch wins with its heart, humor, and one hell of a cast. The movie doesn’t ask much from the viewer rather than to be entertained by Aniston and Bateman and maybe pick up some inspiration along the way. The Switch is a feel-good romantic comedy in the classic sense, the way they don’t make them anymore.
6. Obvious Child
Release Year: 2014
Written By: Gillian Robespierre
Directed By: Gillian Robespierre
Starring: Jenny Slate, Jake Lacy, Gobby Hoffman, Gabe Liedman, Polly Draper, Richard Kind, David Cross
You probably haven’t heard of Obvious Child, but you most definitely have seen its star Jenny Slate pop up in more than a few of your favorite shows. In Parks and Recreation, Slate brought one-half of the spoiled Saperstein kids to life. In Girls, she played Hannah’s arch rival Tally Schifrin. Slate also appeared in Kroll Show, Married, and House of Lies among others.
But with Obvious Child, Slate stands out in the leading role. The romantic comedy finds stand-up comedian Donna (Slate) pregnant after a one-night stand with Max (Jake Lacy). But where this romantic comedy about unplanned pregnancy differs from others like Juno and Knocked Up lies in Donna’s decision to have an abortion.
Obvious Child opened at the Sundance Film Festival, where it was met with overwhelming praise for the subject matter and Slate’s performance. The film’s combination of heavier topics and hilarious humor earned it two Independent Spirit Awards and Slate a Critics’ Choice Award. Obviously, there’s something to love about Obvious Child.
5. The First Wives Club
Release Year: 1996
Written By: Robert Harling
Directed By: Hugh Wilson
Starring: Diane Keaton, Better Midler, Goldie Hawn, Maggie Smith, Dan Hedaya, Bronson Pinchot, Marcia Hay Harden
Remember when Jennifer Lawrence won her Golden Globe for Silver Linings Playbook in 2013 and joked “I beat Meryl!” upon acceptance? Well, she had, in fact, beat Meryl Streep (who had also been nominated for Hope Springs), but the erstwhile Katniss Everdeen was also quoting the legendary comedy film The First Wives Club.
Starring the knockout trio of Diane Keaton, Better Midler, and Goldie Hawn, The First Wives Club follows three women scorned by their husbands after they trade in their wives for newer models. Since they each played a hand in helping their husbands gain success, they won’t accept being dumped. Instead, they decide to get revenge.
It’s no wonder that the surprise box office hit has an enduring cult following (which happens to include one of the most famous movie stars on the planet). For years, there have been rumblings of a sequel to the film taken on a second life in a musical production and will soon become a TV Land comedy series starring Alyson Hannigan, Megan Hilty, and Vanessa Lachey. See where The First Wives Club fandom began or relive an old favorite!
4. Bachelorette
Release Year: 2012
Written By: Leslye Headland
Directed By: Leslye Headland
Starring: Kirsten Dunst, Isla Fisher, Lizzy Caplan, James Marsden, Kyle Bornheimer, Rebel Wilson, Adam Scott
Fan of Kirsten Dunst? Fan of Isla Fisher? Fan of Rebel Wilson? Well, does Amazon Prime Video have the flick for you. From producers Will Ferrell and Adam McKay (who don’t need introducing at this point), Leslye Headland’s Bachelorette stars Dunst, Fisher, and Lizzy Caplan as a group of a troubled trio who gather for the nuptials of an old friend (Wilson).
Like its fellow rowdy R-rated–and often male-led–comedies such as The Hangover and most movies starring Seth Rogen and Jonah Hill, Bachelorette portrays its leads as highly unlikable but lovable nonetheless. As they destroy their friend’s wedding (and themselves), they face their demons in the ruins of the raucous bachelorette party.
The film boasts an unbeatable cast led by the delightful Kirsten Dunst like we’ve never seen her before. Unapologetic, brash, and painfully funny, Bachelorette is must-watch for anyone who loved Bridesmaids but craves even more bite.
3. Almost Famous
Release Year: 2000
Written By: Cameron Crowe
Directed By: Cameron Crowe
Starring: Billy Crudup, Frances McDormand, Kate Hudson, Jason Lee, Patrick Fugit, Anna Paquin, Fairuza Balk, Noah Taylor, Philip Seymour Hoffman
From Cameron Crowe, writer-director of such box office hits as Jerry Maguire and Elizabethtown, the 2000 instant cult classic Almost Famous spoke to a generation of diehard music fans with a touching semi-autobiographical story. Although not a whirlwind commercial success, the film racked up critical praise and a few accolades.
Almost Famous follows teenager William (Patrick Fugit) as he tags along with a budding new rock band’s tour to write an article for Rolling Stone magazine. In the midst of the tour, he strikes up friendships with the lead guitarist Russell (Billy Crudup) and loyal “Band-Aid” Penny (Kate Hudson). It’s a funny and poignant coming of age story set in the world of music. What could be better?
The film took home two Golden Globes–Best Picture and Best Supporting Actress for Kate Hudson–and picked up four Academy Award nominations, taking home one Oscar for writing. Almost Famous has left a lasting legacy on pop culture and remains among Crowe’s best films.
2. Before Sunrise
Release Year: 1995
Written By: Richard Linklater and Kim Krizan
Directed By: Richard Linklater
Starring: Ethan Hawke, Julie Delpy
The first entry in Richard Linklater’s Before trilogy, Before Sunrise, kicks off of the most beloved arthouse film series in recent memory. Trading a massive production, a by-the-book script, and an overfilled supporting cast, Linklater’s romantic dramedies opt for a loose structure, raw emotion, and a palpable realism.
Ethan Hawke and Julie Delpy star as Jesse and Celine, a pair of strangers who meet on a Vienna train and allow their chance meeting to lead them away. They spend the remainder of their time together roaming around Vienna and engaging in an enthralling back-and-forth dialogue. It’s crazy how compelling and completely romantic a movie about two people walking and talking can be.
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After watching the blossoming of Jesse and Celine’s relationship in Before Sunrise, be sure to catch 2004’s Before Sunset (which also happens to be available to stream for free on Amazon Prime) and the latest film, 2013’s Before Midnight.
1. Legally Blonde
Release Year: 2001
Written By: Karen McCullah Lutz and Kirsten Smith
Directed By: Robert Luketic
Starring: Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis, Victor Garber, Holland Taylor, Ali Larter, Linda Cardellini, Jennifer Coolidge
We know it, we love, and it easily tops our list of the best comedy movies available to stream for free on Amazon Prime Video. Legally Blonde, Reese Witherspoon’s star-making breakthrough role, hit the big screen in 2001 and has attained classic status as far as romantic comedies are concerned.
Starring as the bubbly and clueless sorority president Elle Woods, Reese Witherspoon brings the charming character to life from her signature vibrant pink attire to her shining blonde hair. When Elle’s boyfriend dumps her in favor of Harvard Law School, Elle transfers to the prestigious university to win him back. Along the way, she discovers a new sense of self and a love of the law.
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Some 15 years after its release, the film aces the test of time while gently throwing us back to the early aughts. With an excellent supporting cast and its prominence as one of the most quotable comedies of the new millennium, you must add Legally Blonde to the top of your Amazon must-list immediately. What, like it’s hard?