Every month, our contributors submit lists of ten films fitting certain topics. Each month, we feature an alphabetical list of films along with commentary explaining our selections. There will also be an itemized list at the end of each of our individual selections.

We take a comedy break this month between our lists of favorite individual performances. They say drama is easy and comedy is hard. There’s also a fine line between crass and humorous and that line can be crossed without sacrificing comedic value. These films, while many are quite traditional, also feature some obscure films that some may not have seen. Our contributors put together a list of their favorite films. Four films appear on two lists, but none appear on three or more. That gives us a total of 36 films to look at this month.

The four films that were cited twice are Auntie Mame, The Awful Truth, Bringing Up Baby, and Dr. Strangelove, all from prior to the 1970s when comedy began morphing thanks in some small part to films like these four, especially Dr. Strangelove. Of the directors most frequently cited, George Cukor comes out on top with three titles on the list: Dinner at Eight, The Philadelphia Story, and The Women. Three other directors place two titles on the list. Joel Coen (ostensibly with brother Ethan Coen even if not credited such on the two films listed, Fargo and Raising Arizona), Woody Allen (a surprising pair of films: Manhattan Murder Mystery and Midnight in Paris), and Billy Wilder (two of his most famous and popular: The Apartment and Some Like It Hot).

After the break, dig into our setups and follow that by reading about each film.

The Introductions

Wesley Lovell: When picking my films for this list, I tried to go for films that were quite funny and have tickled my funny bone consistently since their releases. Some I’ve seen dozens of times, some I can still remember after having only seen them once. You’ll see a couple of films that regularly have made my lists plus a handful that are entirely new. I’ve gone for obscure and familiar in equal measure, but all have been wonderfully amusing.
Peter J. Patrick: It’s always a chore narrowing down these lists to just ten. Comedies have been with us for as long as there have been theatrical performances. Their movie counterparts go back to the dawn of filmmaking. I have tried to encompass as many eras of film comedy as I could with the limited number of choices and thus chose representative comedies, one each from the 1940s, 1950s, 1970s, 1980s, 1990s, and 2000s, with two each from the 1930s and 1960s. I have chosen ten films with strong narratives, films I can and have watched over and over, most of which can be referred to as dramedies, rather than out-and-out yuck fests.
Tripp Burton: I covered a lot of these movies on the Films I Watch Over and Over Again list, so a lot of this feels redundant. Still, these are the movies that tend to make me laugh the hardest and bring the biggest smiles to my face. And I promise I will try not to just list a bunch of great moments from each of these films!
Thomas LaTourrette: When I was first making up this list, I realized that almost all of the films on it were made between 1937 and 1950. I had not realized how much I admire those early screwball comedies until I saw the list. Figuring that I needed a larger range of films, I have spent a lot of time coming up with a broader set of films. 1937, 1938, and 1939 still have a film each in the list, but they have been joined with films from 1925 through 2011. Once I had enlarged the list, it did become hard to winnow it back down. It was hard to drop such classics as Harvey, Arsenic and Old Lace, and His Girl Friday and more modern films like Moonrise Kingdom and Fargo from the list. I am happy with the result, but I was surprised to find out how difficult it was to limit it to ten.

Airplane! (1980)

(dir. Jim Abrahams, David Zucker, Jerry Zucker) Commentary By Tripp Burton – In terms of jokes per minute, no film can top the dense spoofery of Airplane! What is most miraculous is that most every joke works. This is a hilarious film, not only in how it is written and directed, but by a cast of great actors who never let themselves in on the joke and play every ridiculous moment completely straight mixed in with some underrated comedians playing up every bit of schtick. This is comedic gold.

The Apartment (1960)

(dir. Billy Wilder) Commentary By Peter J. Patrick – Wilder’s remarkable film walks a thin line between comedy and near-tragedy as Jack Lemmon’s office clerk on the rise who loans out his apartment key to his bosses for extramarital liaisons goes from schlemiel to mensch during the film in which Shirley MacLaine as the object of his affection also smartens up after a harrowing suicide attempt. Alternately cynical and tender, this is Wilder’s most accomplished work in a career filled with masterpieces. Years ahead of its time, Wilder thought he would have to turn his script into a play because the production code would not allow it to be filmed. How lucky we are that he was so wrong about that.

Auntie Mame (1958)

(dir. Morton DaCosta) Commentary By Wesley Lovell – There’s a reason this humanistic comedy appears on so many of my lists. It’s a great film with superb performances and wonderful philosophical life lessons to teach. What makes it most fitting to this list is that it’s so uproariously funny that you can’t help but laugh through most of it. Rosalind Russell’s pure wit, charming timing, and acting superiority elevate every frame.

Commentary By Peter J. Patrick – Patrick Dennis’s irrepressible aunt remains everyone’s favorite relative all these years later. Although the film doesn’t quite overcome its stage origins, the laughs come so fast and furiously you don’t mind that you’re essentially watching a filmed stage play. Rosalind Russell in a career-topping performance as Mame leads the way, but she is supported by a superb group of co-farceurs that includes Coral Browne as Vera Charles, Peggy Cass as Agnes Gooch, Henry Brandon as Acacius Page, Fred Clark as Mr. Babcock, and Willard Waterman and Lee Patrick as the Upsons chief among them. Screen joy doesn’t get any better than this.

The Awful Truth (1937)

(dir. Leo McCarey) Commentary By Peter J. Patrick – Twice filmed before in 1925 and 1929, and again in 1953, McCarey’s take on Arthur Richman’s play is so fresh and alive that it belies its origins, looking and sounding as though it were a one-of-a-kind concoction between its director and co-star Cary Grant who sprang to superstardom essentially playing McCarey opposite Irene Dunne at her most luminous. Both Grant and Dunne have scenes in which they seem to be making it up as they go along, but Grant and the playful hat trick scene with the dog and Dunne and her fake drunk scene were both scripted. Never has love, marriage, divorce and rediscovery been done so brilliantly or so hilariously.

Commentary By Thomas La Tourrette – A screwball comedy, pairing Cary Grant and the peerless Irene Dunne. They play a couple who may not be perfect for each other, but who find life without the other awfully dull. The film was probably a bit racy for 1937, with hints of marital infidelity, but that didn’t stop it from winning one Oscar and being nominated for five more.

The Birdcage (1996)

(dir. Mike Nichols) Commentary By Tripp Burton – La Cage Aux Folles is a story that has been told many times in many different formats, but Mike Nichols’ American film version is the funniest by far. An all-star cast all at the top of their game — from Robin Williams and Nathan Lane to Dianne Weist and Gene Hackman to Christine Baranski and a shoeless Hank Azaria — takes Elaine May’s witty script and goes to town with it, layering on joke after joke. It is infinitely quotable, with a heart beneath it that makes its characters all the funnier.

Bringing Up Baby (1938)

(dir. Howard Hawks) Commentary By Tripp Burton – Bringing Up Baby is the quintessential Screwball comedy, my favorite genre of comedy. It takes everything that makes the genre great — mistaken identities, stuck-up rich folk, free spirits, and utter confusion — and chases it around with a couple of wild leopards. The cast is excellent, led by a hilarious Katharine Hepburn who was never funnier and a dapper Cary Grant who was never more chaotic, and the way Howard Hawks keeps the dialogue and film moving at a breakneck speed and never lets up.

Commentary By Thomas La Tourrette – Perhaps the classic screwball comedy. Katharine Hepburn plays an heiress who falls in love with a paleontologist played by Cary Grant. Add a couple leopards, a bone-stealing dog, a torn lame gown and a visit to the county jail and you have the makings of one of the funniest films ever made.

Broadcast News (1987)

(dir. James L. Brooks) Commentary By Peter J. Patrick – Brooks achieved TV immortality with the comedy classic The Mary Tyler Moore Moore Show, two of its three off-shoots (Rhoda, Phyllis), and the equally hilarious Taxi, as well the MTM dramatic offshoot Lou Grant before the multi-Oscar-winning Terms of Endearment established him for a short time as one of the screen’s preeminent writer-producer-directors. His hilarious big-screen take on TV news with Broadcast News was no surprise, with William Hurt, Holly Hunter, Albert Brooks, and briefly Jack Nicholson all at the top of their games.

Butterflies Are Free (1972)

(dir. Milton Katselas) Commentary By Peter J. Patrick – More in tune with the late 60s than the early 70s, this film of the hit Broadway play that captured audience’s hearts as it tickled their funny bones in regional theatres across the country as well as on the Great White Way, benefits from the relocation to San Francisco and the star wattage of Goldie Hawn at her brightest as the kooky neighbor, Edward Albert at his freshest as the blind boy attempting to strike out on his own, and the superb Eileen Heckart as his overprotective mother. Every actress of a certain age campaigned for Heckart’s role, but the veteran Broadway star was thankfully allowed to recreate her stage triumph on screen.

Clue (1985)

(dir. Jonathan Lynn) Commentary By Wesley Lovell – This is another film that regularly appears on my lists. It’s not only genuinely funny, but it’s the film I’ve seen most often. When I’m feeling blue or need a quick diversion, Clue is the film I turn to. It features some of the masters of comedy doing their absolute best putting on a live performance of the adventures of my all-time favorite board game.

Dinner at Eight (1933)

(dir. George Cukor) Commentary By Peter J. Patrick – Frances Marion and Herman J. Mankiewicz adapted Edna Ferber and George S. Kaufman’s stage hit for the screen, putting their own spin on it, making it even funnier. Although the film includes the tragic death of a major character and the impending death of another, it never strays too far from its comedic center. Grand Hotel may have been the first all-star cast film, but this was the first to integrate almost its entire cast into one scene, the fabulous last one. That brilliant cast includes Marie Dressler, John Barrymore, Jean Harlow, Wallace Beery, Lionel Barrymore, Billie Burke, and Lee Tracy, all at their shimmering best.

Dr. Strangelove (1967)

(dir. Stanley Kubrick) Commentary By Wesley Lovell – Stanley Kubrick excelled at every genre he tackled: costume dramas, war films, science fiction, horror, and even comedy. Dr. Strangelove was a brilliant satire featuring three unparalleled performances by a single actor: Peter Sellers. The absurdist comedy has never lost its edge after 50 years and its biting political commentary is still as pointed and fitting now as it ever was.

Commentary By Tripp Burton – Stanley Kubrick was never a filmmaker you thought of when you thought of funny. Many of his greatest films feel almost humorless through most of their runtime. It is remarkable, then, that he made one of the funniest, most chaotically satiric films of all time. Dr. Strangelove owes a lot to Peter Sellers, in one of the greatest comedic feats of all time playing three radically different roles, and an ensemble of actors who were never funnier than playing with material this inspired. But Kubrick also gives it just the right touch, letting the stakes feel so dire that the humor becomes that much more ridiculous.

Easy A (2010)

(dir. Will Gluck) Commentary By Wesley Lovell – The film that introduced us to Emma Stone is so much more than that. It’s a touching, modern comedy about a young woman who accepts the taunts she’s given from her classmates, embraces them, and turns it all against them. While being fiercely determined, she’s also internally frustrated by the whole affair. Supported with wonderful performances by Patricia Clarkson and Stanley Tucci, there is no question that Stone commands the film in a performance that should be talked about for generations.

Fargo (1996)

(dir. Joel Coen) Commentary By Peter J. Patrick – The Coen Brothers had been making thrillers tinged with comedy for over a decade. Initially both Joel and Ethan were credited with writing them, but only Joel was credited with directing. Ethan has since been unofficially retroactively credited with co-direction on all of them. Although classified as a crime drama, it is impossible to fully appreciate Fargo unless you look at it as a comedy, a very dark comedy in which people are murdered in the most gruesome ways. It can also be viewed as a feminist mystery in that its heroine is a very pregnant, yet resourceful cop, played by Joel’s wife Frances McDormand who won an Oscar for it. She’s in good company with William H. Macy, Steve Buscemi, Harve Presnell, et al.

The General (1926)

(dir. Clyde Bruckman, Buster Keaton) Commentary By Tripp Burton – No Favorite comedies list can exist without some silent comedy, the best of which holds up against anything modern in terms of big laughs. I could have filled this list with [Charlie] Chaplin and [Harold] Lloyd films, but instead I picked Buster Keaton’s The General, a tense, hilarious, and consistently awe-inspiring epic comedy. The laughs in this film come more from the amazement of the risks that Keaton is taking, although that also diminishes the skill with which Keaton composes his set pieces. He was a master, and this might be his masterpiece.

The Gold Rush (1925)

(dir. Charles Chaplin) Commentary By Thomas La Tourrette – Charlie Chaplin was a great physical comedian, and he is in prime form when the little tramp goes to Alaska during the gold rush. A scene where strong winds keep blowing people straight through a house still stands as a brilliant set piece. Certain parts may not hold up as well, but it stands as one of his triumphs as actor, writer, and director.

It Happened One Night (1934)

(dir. Frank Capra) Commentary By Wesley Lovell – Frank Capra’s clever romantic comedy is a superbly crafted film about a newspaper reporter and a spoiled heiress as they travel across the country trying to escape her domineering father. Claudette Colbert and Clark Gable deliver fine performances, but it’s the astute and humorous script by Robert Riskin that makes the film a success.

Kind Hearts and Coronets (1949)

(dir. Robert Hamer) Commentary By Wesley Lovell – This is one of those comedies that those who’ve seen it remember fondly, which seems like a small group of people. Alec Guinness takes on nine roles, all of them members of the same aristocratic family that disowned the protagonist’s mother when she married below her station. One by one, they are all killed. The film is a dark, but glorious comedy with Guinness in a role that is easily among his best.

Love Actually (2003)

(dir. Richard Curtis) Commentary By Peter J. Patrick – Rarely do films comprised of vignettes in which people appear with only the vaguest of connections to the people in other vignettes work, but this British comedy set in the months before and after Christmas really does. The all-star cast, all of whom either fall in or out of love, includes Hugh Grant, Emma Thompson, Alan Rickman, Laura Linney, Colin Firth, Liam Neeson, Bill Nighy, Chiwetel Ejiofor, Keira Knightley, and Andrew Lincoln. “Love Is All Around” with Grant as the new Prime Minister, Thompson his sister, Rickman her husband, and so on. Billy Bob Thornton makes a brief appearance as the visiting U.S. President.

Manhattan Murder Mystery (1993)

(dir. Woody Allen) Commentary By Tripp Burton – Woody Allen, one of my favorite filmmakers, has made a slew of comedies that I adore. There is something eminently rewatchable about this underseen comedy of his, though, and I had to cite it on this list. It is one of Woody’s more outrageous set-ups, with he and Diane Keaton (filling in for a mid-breakup Mia Farrow) convinced that their neighbor has murdered his wife and getting entangled in a plot that seems more and more plausible the more and more ridiculous it gets. The actors, including Alan Alda and Anjelica Huston, are in top form and it creates one of Woody’s most quotable comedies.

Midnight in Paris (2011)

(dir. Woody Allen) Commentary By Thomas La Tourrette – A later entry by Woody Allen. Owen Wilson plays a modern day writer who thinks life was better in the 1920s in Paris. A magic cab can take him back where he falls in love with a woman who assumes that life in the Belle Epoque would be better than her present life. It shows that nostalgia can overwhelm one’s present and make one wistful for a better time, but it has a lot of laughs along the way.

The More the Merrier (1943)

(dir. George Stevens) Commentary By Peter J. Patrick – The World War II Washington D.C. housing shortage provided the impetus for this wonderful romantic comedy featuring Jean Arthur and Joel McCrea as the initially bickering roommates made for each other and Charles Coburn as their indefatigable matchmaker. Stevens’ penchant for not rushing scenes, for allowing actors to develop their characters naturally, goes a long way in making the three leads unforgettable in what was then a brief contemporary situation. It still works, even though the 1966 attempt at recapturing it at the 1964 Tokyo Olympics in Walk Don’t Run fails miserably despite having Cary Grant as its matchmaker.

Mother (1996)

(dir. Albert Brooks) Commentary By Wesley Lovell – Albert Brooks made a handful of humorous comedies in the 1990s. Among the best was this gem about he and his spitfire mother (Debbie Reynolds). Reynolds gives the performance of her career as Brooks’ perfectionist mother. It is a comedy of unvarnished humor and astute observations about the mother-son dynamic.

Murder by Death (1976)

(dir. Robert Moore) Commentary By Wesley Lovell – Neil Simon’s sharply written comedies, stage and film, are exercises in witty wordplay and zany, madcap adventure. Never was this more bizarrely framed than in his 1976 mystery comedy. Starring a who’s who of noted actors, we are introduced to simulacrums of the world’s greatest detectives, invited to a dinner party where their wealthy host hopes to stun them into failure with myriad tricks and ruses. It’s an incredibly funny comedy and deserves more broad recognition than it currently enjoys.

The Opposite of Sex (1998)

(dir. Don Roos) Commentary By Wesley Lovell – Christina Ricci and Lisa Kudrow have seldom been better than in this off-beat comedy about a 16-year-old girl who seduces her gay half-brother’s boyfriend. It’s been almost twenty years now since I last saw this film, but it’s one I fondly remember adoring at the time and would more than happily pop in again just to relive the entertainment.

The Philadelphia Story (1940)

(dir. George Cukor) Commentary By Thomas La Tourrette – This film ends up on many of my lists, but it is a superb comedy. Katharine Hepburn, Cary Grant, Jimmy Stewart, and Ruth Hussey have some of the best roles of their careers in this film. The stage play was written for Hepburn by Philip Barry, but Donald Ogden Stewart improved the writing for the screen and won an Oscar for doing it. Hepburn shines in the tailor-written role, but the whole cast is superb and the dialogue sparkles. I just watched it again in preparation of writing this and found I still loved it.

Playtime (1967)

(dir. Jacques Tati) Commentary By Tripp Burton – Playtime is the only film on this list I have only seen once, but it was in a packed theater, projected on 70mm, and I have never seen more people beam with happiness at one time. You could sense the joy in the theater at every turn. Jacques Tati made films that may have been funnier, but this is so joyous, clever, and infectious that you can’t help but love every moment of it. It is a crowning achievement of filmmaking.

The Princess Bride (1987)

(dir. Rob Reiner) Commentary By Thomas La Tourrette – One of the funniest comedies of recent years, this one holds up to repeated viewings. William Goldman adapted his own book into a very different, but still incredibly funny, film. A perfect cast from small roles, like Peter Cook as The Impressive Clergyman to the improbably good looking Cary Elwes who was the right Wesley, brings the film to life. It contains multiple quotable lines and holds its own among comedies.

Raising Arizona (1987)

(dir. Joel Coen) Commentary By Tripp Burton – The Coen Brothers have made a lot of movies that could be on this list, but I love none of their comedies the way I love Raising Arizona. It is outrageous and humane at the same time, loving these ridiculous characters while basking in their grotesqueness. It contains one hilarious set piece after another, and is both verbally and visually as funny a film as these comic genius’ have put together.

The Royal Tenenbaums (2001)

(dir. Wes Anderson) Commentary By Tripp Burton – I can run hot and cold on Wes Anderson, but The Royal Tenenbaums may be his hottest film in my book. Using a top-notch ensemble of great personalities and a series of ridiculous turns, Anderson turned this family saga into his funniest film. In fact, the characters are so warm and loveable that this is a film that gets funnier with each revisit, while also getting deeper and more touching.

Some Like It Hot (1959)

(dir. Billy Wilder) Commentary By Thomas La Tourrette – There is a reason why this tops the list of the AFI’s list of best comedies. Jack Lemmon and Tony Curtis play musicians who hide by going in drag and playing in a band with singer Marilyn Monroe. They try to stay hidden from gangsters along the way, but also fall in love. A besotted Joe E. Brown has the classic closing line of the film, but the whole cast shines throughout.

Tom Jones (1963)

(dir. Tony Richardson) Commentary By Peter J. Patrick – Henry Fielding’s bawdy 1749 novel was devoured by the British masses upon publication and has remained in print ever since. Richardson’s film version was just as bawdy, opening up a new screen modernism and sense of sexual freedom that helped usher in the swinging 60s. Audiences laughed uncontrollably at the then-shocking promiscuity on display in a mainstream film. Though hardly shocking today, there is still plenty to make you laugh in John Osborne’s droll screenplay and the deft performances of Albert Finney, Susannah York, Hugh Griffith, Edith Evans, Joyce Redman, Joan Greenwood, Diane Cilento, Lynn Redgrave, and others.

Tootsie (1982)

(dir. Sydney Pollack) Commentary By Wesley Lovell – Dustin Hoffman plays a difficult actor who must take on a female guise in order to secure work. Hoffman’s cross-dressing star Dorothy Michaels takes on a life of her own becoming a celebrated performer. Hoffman is superb, but is wonderfully supported by the likes of Jessica Lange, Teri Garr, Dabney Coleman, Bill Murray, Charles Durning, George Gaines, and Geena Davis. The humor is uproarious and the film is fun in its over-the-top way.

Victor/Victoria (1982)

(dir. Blake Edwards) Commentary By Thomas La Tourrette – This was a runner-up in my list of best musicals, but it fits here as well. A down on her luck singer played by Julie Andrews is taken under wing by Robert Preston who has a grand time playing a gay cabaret singer. I may not totally buy Julie Andrews as a man, but she was a hoot with the whole cast as she becomes the toast of the town as Victor. Blake Edwards had a deft hand as writer and director of this gem.

What’s Up, Doc? (1972)

(dir. Peter Bogdanovich) Commentary By Tripp Burton – Peter Bogdanovich’s throwback to screwball comedies, and loose remake of Bringing Up Baby at the same time, is a film that I seem to love more than anyone else. It is hilarious, though, with a deep bench of comedic character actors and a deeper bench of well-crafted gags and set pieces. It all culminates in the funniest chase scene in history, that shows off both San Francisco and it’s cast of game comedians at the same time.

The Women (1939)

(dir. George Cukor) Commentary By Thomas La Tourrette – A gaggle of A-list actresses inhabit this funny film. Norma Shearer and Joan Crawford battle for the same man with strong support from Rosalind Russell, Paulette Goddard, and Marjorie Main among many others. George Cukor was known as a “women’s director” and he proves he can live up to that with a cast of only women.

Young Frankenstein (1974)

(dir. Mel Brooks) Commentary By Thomas La Tourrette – In my mind, this is Mel Brooks’ finest film. It is a great send-up of the Frankenstein films, filmed in glorious black-and-white. Gene Wilder fronts one of the best casts with amazing turns by Teri Garr, Madeline Kahn, and Cloris Leachman to name just three of the supporting cast. Life in Transylvania was never more amusing.