In honor of me turning 30, I’m compiling 30 different top-30 lists on a wide variety of topics ranging from trivial interests of mine to meaningful life moments. Read the introductory post for more background information on my 30 at 30 project. Reminder: there is no scientific rationale for these lists. They were composed by a panel of one—me.
I don’t watch a lot of movies, at least not compared to some of my family and friends who are true movie buffs. When Oscar season rolls around, I’m usually left scratching my head wondering how it’s possible that I never heard of so many of the nominated films. When it comes to on screen entertainment, I spend the vast majority of my time watching sports. I also regularly watch a substantial number of TV shows. While sports and TV shows are a part of my day-to-day life, movies are more of a rare treat reserved for special occasions.
I could probably count on one hand the number of times I have been to the theater in the past year, and when I tried to remember back to the last movie I saw at the theater, I was stumped. Maybe Trainwreck in 2015? Jessie and I occasionally watch something on Netflix or HBO Go, and we make a few trips to Redbox or Family Video to catch up on some of the movies we missed, but the truth of the matter is that there are a lot more movies that I don’t see than ones that I do see these days.
When it comes to movie preference, I generally prefer something lighthearted and funny. So don’t expect my list of favorites to mirror IMDB or Rotten Tomatoes. My list has nothing to do with critical acclaim and everything to do with appealing to me. Nonetheless, if you haven’t yet seen any of the 30 movies on my list, I highly recommend checking them out. Each one of them is a movie that I could and have watched multiple times. Now without any further ado, my favorite 30 movies of all-time. I also included links to each movie’s IMDB page in case you are interested to learn more:
30. Toy Story (1995)
While 2010’s Toy Story 3 hit everyone in my generation (myself included) right in the feels, I have to give the nod to the original Toy Story movie that introduced the world to Woody, Buzz, and the gang of talking toys. The Pixar animation was revolutionary at the time, and the story was so good it earned an Oscar nomination for “Best Writing, Screenplay Written Directly for the Screen.” As a “kid’s movie” that also played to adults, this movie lives on “to infinity and beyond!”
29. Meet the Parents (2000)
Ben Stiller is exactly the kind of goofball comedic actor that I typically enjoy. Although I would rank him behind the likes of Will Ferrell, Adam Sandler, and Steve Carell, Stiller has made a career out of being a buffoon. My brother Mike is as big of a Ben Stiller fan as I know, and surely he will be disappointed to see that other Stiller projects like Zoolander, Dodgeball, and Starsky & Hutch did not crack my top 30. Neither did There’s Something About Mary, though it would have made the honorable mentions if I included them. However, Stiller’s role as Gaylord Focker in Meet the Parents is my personal favorite Ben Stiller movie. I also love Robert DeNiro showing off his comedic chops as Jack Byrnes, the suspicious former CIA would-be father-in-law.
28. Talladega Nights: The Ballad of Ricky Bobby (2006)
Will Ferrell is my favorite comedic actor. From his legendary work on Saturday Night Live to his career in Hollywood to his appearances on late night television, Ferrell is always good for a laugh. As NASCAR driver Ricky Bobby, Ferrell teamed with John C. Reilly in a movie that is forever quotable. From “Shake and bake!” to “If you ain’t first, you’re last” to “Dear 8 pounds 6 ounces… newborn infant Jesus, don’t even know a word yet…” Talledega Nights has no shortage of memorable lines.
27. Step Brothers (2008)
Speaking of memorable lines, Step Brothers, another movie starring Ferrell and Reilly, is full of them. The whole Prestige Worldwide scene is hilarious, but my personal favorite scene is when they interview for a job and have the great Pam/Pan conundrum. I don’t even know why, but that little scene makes me laugh out loud every time. Also, the bunk bed scene is a gem: “so much extra space in our room to do activites!”
26. Dan in Real Life (2007)
Although it was not nearly as big of a hit as some of Steve Carell’s other projects, Dan in Real Life has a humanness to it that I really enjoyed that goes beyond the humor. Bonus points for a top notch soundtrack from Sondre Lerche.
25. Napoleon Dynamite (2004)
Napoleon Dynamite was weird, and I loved it. When it came out in 2004, it felt retro and new at the same time. It was hard to tell if it was made in 1984 or 2004. The characters spoke and acted oddly. The soundtrack was unique. The deadpan comedy was unlike anything I had ever seen before, and while some people watched it and responded like the farmer when Napoleon asked if the chickens had large talons, I went back and re-watched it again and again. Vote for Pedro!
24. Love & Basketball (2000)
How do you get teenage me interested in a romantic film? The answer is simple: basketball. I loved the tagline of “All’s fair in love and basketball” and dreamed of a day when I would play a similarly high stakes game of one-on-one.
23. The Dark Knight (2008)
Batman has always been my favorite superhero. I grew up watching reruns of the old 1960s Adam West Batman TV series and enjoyed watching all of the Batman movies growing up, but in my opinion, The Dark Knight is the best Batman movie to date. Led by Heath Ledger’s Oscar-winning performance as The Joker, The Dark Knight is the most action-packed Gotham film yet.
22. Memento (2000)
I first watched Memento as part of a class requirement for a Psychology Through Film class that I took as a freshman at Mercyhurst College. It was my favorite movie that we watched as part of the course. The film’s unique storytelling really forced the viewer to pay careful attention trying to piece together the plot as it unraveled.
21. Freedom Writers (2007)
Based on Erin Gruwell’s book The Freedom Writers Diary, this movie tells the inspiring story of a group of inner-city students and their teacher. Of course I know that the real world has a lot of ways of preventing a happy Hollywood ending. Nonetheless, as an educator, I believe everyone can take away some important lessons from this movie, particularly the value of having teachers who believe in their students and the importance of getting young people to write.
20. Coach Carter (2005)
There are certainly some parallels between Freedom Writers and Coach Carter. Both are based on true stories. Both are inspiring tales of overcoming the odds and young people triumphing in the face of adversity with the help of a stubborn, determined teacher/coach. One of the most powerful moments of the movie comes when one of Carter’s players, Timo Cruz, speaks up to recite a secularlized version of a powerful Marianne Williamson quote that begins, “Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure.”
19. Rocky III (1982)
Rocky III is only movie to make my list that was released before I was born. While I enjoyed each of the first four Rocky movies, Rocky III was always my favorite for one simple reason: Thunderlips! I was a huge Hulk Hogan fan growing up, and his presence in Rocky III drew me into the story more than even Sylvester Stallone and Mr. T.
18. The Mighty Ducks (1992)
Gordon Bombay is the best fictional coach in movie history. That’s a fun debate starter. Regardless of where you come down on Bombay’s coaching prowess, this movie is a delightful kids movie. I dare you to watch and not root for Charlie, Fulton, Goldberg, and the rest of the gang to get the win. With my apologies to The Sandlot, Little Giants, and all of the other kids sports movies out there, The Mighty Ducks is my top choice. Quack quack quack, Mr. Ducksworth!
17. Tommy Boy (1995)
Of all the stars Hollywood lost too soon, Chris Farley may have been its biggest loss—literally and figuratively. The SNL alum was only 33 years young when he died in 1997. Of the few films Farley starred in, Tommy Boy is my personal favorite. David Spade serves as the perfect straight man to play next to Farley’s over-the-top physical comedy. And “fat guy in a little coat” is the stuff of legend. The duo had similar success the following year with Black Sheep. Sadly, Farley would appear in only three more films before his untimely passing due to a cocaine and morphine overdose.
16. I Love You, Man (2009)
Poor Peter Klaven (Paul Rudd) has no male friends, which becomes a problem when he gets engaged to be married. In search of a best man, he meets Sydney Fife (Jason Segal). The two have instant chemistry and quickly becomes close friends to the point where their friendship becomes a threat to Peter’s engagement. The chemistry between Rudd and Segal is palpable, and their interactions resulted in multiple laugh out loud moments for me. I especially enjoy all of Peter’s flubbed lines when trying to sound cool to Sydney.
15. Donnie Darko (2001)
And now for something completely different, a drama/sci-fi/thriller. Donnie Darko is strange. It’s alluring. I guess it makes sense that I liked this movie in the same way that I enjoyed Memento. There are a lot of missing pieces to try to put together exactly what is happening in this movie and why. Young Jake Gyllenhaal plays the title character, a troubled teenager who may be suffering from mental illness.
14. Aladdin (1992)
The Lion King is probably my runner-up pick when it comes to Disney movies, but Aladdin is hands down my favorite Disney movie. To this day I can sing along with most of the songs, and Jessie and I have been known to bust out a mean karaoke duet of “A Whole New World” from time to time. From Robin Williams as Genie to Gilbert Gottfried as Iago, Aladdin features a tremendous cast of voice actors. Clocking in at 90 minutes, it is a fast-moving, action-packed animated adventure that the whole family can enjoy. I look forward to watching it with Ben someday in the future.
13. Office Space (1999)
I don’t remember exactly when I first saw Office Space, but I remember that I gained a new appreciation for the movie after college when I worked my first office job. Though I was never in the doldrums like Ron Livingston’s character Peter Gibbons and never worked for a boss like Bill Lumbergh (Gary Cole), the movie accentuates all of the quirks of working an office life in hilarious fashion. From Peter’s friends at work Samir Nagheenanajar and Michael Bolton (“No way! Why should I change? He’s the one who sucks.”) to his crazy neighbor Lawrence to the poor office doormat Milton, Office Space is filled with amazing characters. Oh yeah, the movie also features Jennifer Aniston as Peter’s love interest. If you have ever worked in an office environment, this movie is a must see.
12. Happy Gilmore (1996)
Adam Sandler in the mid-90s was comedic gold. Three of his movies released between 1995 and 1998 rank in my top 12. The quality of his movies began to slip by the turn of the century, and I haven’t even bothered to see most of the movies he has starred in over the past decade. I think it’s safe to say that I am no longer part of his target demographic. However, Happy Gilmore is another story. In 1996, Happy Gilmore did the impossible for 12-year-old me: it made golf both fun and funny to watch. Sandler’s take on the PGA Tour was hilarious. There is so much to love about this movie: Happy’s fight with Bob Barker, the “jackass!” fan, Chubbs’ arm, Mr. Larson and his “Guns Don’t Kill People, I Kill People” T-shirt, Shooter McGavin’s unusual breakfast of champions. The list could go on and on.
11. Wedding Crashers (2005)
There was a stretch in the mid-2000s when it seemed liked the same group of actors were showing up in each other’s movies every year. Vince Vaughn and Owen Wilson were right at the top of that list, but my personal favorite movies of theirs was Wedding Crashers. While Vaughn and Wilson’s best friend chemistry takes center stage, Will Ferrell’s cameo as Chazz Reinhold cannot be understated. There is a lot of great physical comedy, and the entire sequence with the Cleary family is loaded with laughs.
10. The Social Network (2010)
Facebook launched the same year that I began college. I joined Facebook in 2005 as a sophomore in college. I also started dating Jessie that year. So when the movie The Social Network came out in 2010, it felt like it was documenting not just a moment in history, but a moment in history that coincided with some of the best memories of my life. Writer Aaron Sorkin’s clever screenplay and director David Fincher’s masterful cinematography tell the story in such a captivating way that Jessie and I actually saw this movie in the theaters twice. Jesse Eisenberg earned an Oscar nomination for his leading role as Facebook founder Mark Zuckerberg, and Andrew Garfield was excellent as Zuckerberg’s former best friend Eduardo Saverin. While I am not sure how well this film will age (already, many of my high school students don’t seem to care about Facebook), I believe it will always resonate with me and my generation.
9. Knocked Up (2007)
Seth Rogan’s breakout film, Knocked Up, tells the story of unambitious Ben Stone (Rogan) and career woman Alison Scott (Katherine Heigl). An unlikely hookup leads to an unexpected pregnancy, and the rest of the movie follows their struggle—humorously—to try to make it all work even though it seems like they have very little in common. As much as I enjoy the lead couple, I also get a kick out of the married-with-kids struggles faced by Alison’s sister Debbie (Leslie Mann) and her husband Pete (Paul Rudd). Long before his foray into TV as Dr. Ken, Knocked Up was also the vehicle for a breakout performance by Ken Jeong as the all-too-serious, hysterical Dr. Kuni. His interactions with Rogan and Heigl are among my favorite moments of the movie.
8. Ferris Bueller’s Day Off (1986)
I was much too young to see this movie when it was released, but when I finally did see it at some point in my teenage years, I instantly understood its lasting appeal. Although I was probably much more like Cameron as a high school student, Ferris set the gold standard for “I wish I could do that!” as a kid. From the joyride in Cameron’s old man’s Ferrari to his suave demeanor with Sloane Peterson, Ferris is the coolest. As he says, “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”
7. The Wedding Singer (1998)
I’ve already professed my love for 90s Adam Sandler, but is there a better woman in the romantic comedy lead role than Drew Barrymore? She has the cute girl-next-door role down pat, and her performance here as the would-be Mrs. Julia Gulia is arguably her at her most charming. The Wedding Singer is set in the 1980s, which makes for some fantastic fashion choices as well as a killer soundtrack—and that’s not even including the wedding singer performances by Robbie Hart (Sandler) and his competitors. Also, George is a scene stealer throughout the movie.
6. Dumb & Dumber (1994)
A lot of Jim Carrey films would have made my honorable mentions list, but none of them compares to the comedy classic Dumb & Dumber. The sequels are meh. The original is untouchable. Lloyd Christmas (Carrey) and Harry Dunne (Jeff Daniels) turn dumbness into an art form. It’s one of the most rewatchable movies. There are no wasted scenes, and the laughs just keep coming. There are too many quotable moments to pick from to claim a favorite, but I’ll include this one, which I often quote in my regular life: “Just when I thought you couldn’t possibly be any dumber, you go and do something like this… and totally redeem yourself!” OK, one more: “So you’re telling me there’s a chance. YEAH!”
5. Finding Forrester (2000)
Remember Love & Basketball from earlier on this list? Well, Finding Forrester could be subtitled “Writing & Basketball,” which for me is the next best thing. Sean Connery stars as reclusive writer William Forrester. He meets a young writing prodigy named Jamal Wallace (Rob Brown) who happens to be a promising basketball prospect. Jamal’s basketball talent helps earn him scholarship to a prestigious prep school in Manhattan, but when Jamal applies himself in the classroom and not just on the court, he rubs some prejudiced people the wrong way. The unlikely mentorship/friendship between Forrester and Wallace helps both characters in different ways. The movie also includes one of my favorite quotes about writing, which comes from Forrester, “The first key to writing is… to write, not to think!”
4. Billy Madison (1995)
I don’t have the data to prove it, but if I had to guess I would say that I have watched Billy Madison more than any other movie in my life. It’s one of those movies that, if it happens to be on TV while flipping through the channels on a random Saturday afternoon, I’ll stop and tune in for 20 minutes over lunch. Then, an hour or so later lunch will be long gone and I’ll still be watching. As far as I’m concerned, Billy Madison is Adam Sandler’s magnum opus. I have seen this movie so many times that whenever I watch it, I tend to recite most of the scenes word for word. From Chris Farley’s infamous scene as the zany bus driver to Sandler working his way from first grade through high school, this movie is eminently quotable. One of my favorite lines comes from the principal after Billy tries to wax poetic about the industrial revolution. “Mr. Madison, what you’ve just said is one of the most insanely idiotic things I have ever heard. At no point in your rambling, incoherent response were you even close to anything that could be considered a rational thought. Everyone in this room is now dumber for having listened to it. I award you no points, and may God have mercy on your soul.” I like to use that line anytime someone I know rambles on incoherently.
3. Anchorman: The Legend of Ron Burgundy (2004)
Anchorman just barely outranks Billy Madison as my all-time favorite comedy. This faux biopic of 1970s San Diego newsman Ron Burgundy (Will Ferrell) follows suit of some of the other comedies I have mentioned in being a tour de force of quotability. Ferrell’s over-the-top portrayal of Burgundy as a self-absorbed, naive showman has made him one of the most beloved characters of the 21st century to the point where Ferrell has actually played the character conducting real interviews. The supporting cast deserves a mention as well, particularly Christina Applegate who plays Ferrell’s love interest and co-anchor Veronica Corningstone and the rest of the Channel 4 News Team, Brian Fantana (Paul Rudd), Brick Tamland (Steve Carell), and Champ Kind (David Koechner). The plot of Anchorman is wild and totally unrealistic, but anyone who is taking this movie seriously is watching the wrong movie. Spoiler: I think Brick killed a man with a trident.
2. Garden State (2004)
Garden State was a life-changing movie for me. Zach Braff’s cinematic masterpiece feels epic every time I watch it. Braff was the writer, director, and star of the film. The movie is a coming of age drama centered on Braff’s character, Andrew Largeman, an actor who takes himself off the medication he has been taking for years in an attempt to finally feel something and to live a more genuine, fulfilling life. Natalie Portman plays Largeman’s love interest Sam, a quirky, pathological liar who clearly has issues of her own. The impact of the cinematography and soundtrack cannot be overstated. Watching Garden State is a sensory delight. It is a captivating visual and aural experience. The movie features a litany of poignant quotes, but the one that always hit me the hardest was when Andrew addressed Sam, saying, “…Cause like you said, this is it. This is life. And I’m in love with you… I think that’s the only thing I’ve ever really been sure of in my entire life.” I had an inkling that I felt that way about Jessie, even before I knew what love really meant, and that line always stuck with me.
1. Hoop Dreams (1994)
Only one documentary found its way onto my list of favorite films. Not only did Hoop Dreams make the list, but it has been my favorite film ever since I first watched it more than 20 years ago. When I first saw Hoop Dreams as a kid, I related to it because I had hoop dreams of my own. Similar to subjects of the movie, Arthur Agee and William Gates, I had dreams of growing up to one day play basketball in the NBA. Unfortunately, those dreams fell short for all three of us. However, when I watch Hoop Dreams today, it’s clear that aside from our NBA dreams, our childhood experiences were vastly different. As this documentary follows Agee and Gates throughout their high school years, viewers are privy to the ups and downs of life for two young men and their families. More than a story of two promising basketball prospects from Chicago, Hoop Dreams tells the story of two young African-American men who overcame a variety of obstacles to eventually earn college scholarships playing basketball. Unlike Hollywood, the documentary doesn’t have a fairy tale ending. Ultimately, neither man ever played a minute in the NBA. However, there are some silver linings to the story as explained in Gabriel Baumgaertner’s 2015 article for The Guardian. The documentary runs nearly three hours long, so watching it is a commitment, but if you appreciate good, compelling storytelling, and have even a slight interest in basketball, this is one film you have to watch.