From ‘His Girl Friday’ to ‘Small Time Crooks’: More of the Best Comedies We Have Ever Seen

Posted Friday, September 19, 2025 - 11:11 am
comedies

 

“Comedy is difficult.” So said the great actor Matt Dillon, who once nailed a brilliant and side-splitting performance as the shady private investigator Pat Healy in the classic film, Something About Mary (which our Chief Film Critic Forrest Hartman has included in his list below).

 

Yes, comedy is hard – and only a handful of talented actors can deftly deliver the sharp zingers that the even more talented scriptwriter has written for them.

 

What is it about the art of making audiences laugh that intrigues us so? Perhaps, for most of us, our earliest and fondest on-screen memories were those of comedians who made us laugh -- and still do: from Charlie Chaplin and Buster Keaton, to Elaine May and Jacques Tati, to Richard Pryor and Eddie Murphy, and many others.

 

Even though comedy is no doubt the most popular genre, it has been always shortchanged in the awards circuit – the Oscars, for example, notoriously favor dramas, and always overlook the extreme talents of comedic actors who propel audiences to laughter.

 

But in a multipart series in this magazine – kicked off by Ulises Duenas, Ben Friedman and Garret Hartman -- we plan to right the wrong, and do justice to the art of comedic films, as our Chief Film Critic Forrest Hartman and I hereby rave about the best comedies we have ever seen – and recommend that you watch too.

 

And the clear winner -- the comedy that appeared on almost all of our writers' lists -- is: Ferris Beuller's Day Off. 

 

--Tara Taghizadeh--

 

comedies

--

Tara Taghizadeh, Founding Editor & Publisher:

 

--Small Time Crooks

Yes, I am a Woody Allen fan – I have been since my early youth. It’s safe to say that Allen used to be one of the best American filmmakers around – and God, does he grasp comedy. 

Small Time Crooks may not be as well-known as Annie Hall or his other works, but it’s a gem, about a gang of grifter friends whose get-rich-quick scheme to rob a bank naturally goes awry. 

But somehow, through a bizarre and hilarious twist of fate, they all end up richer than they could ever imagine –with a lot of help from the heroine of this movie, Frenchie (Tracey Ullman), who bakes dynamite cookies.

With a notable cast, starring Allen, Ullman, Jon Lovitz, Elaine May, and Michael Rapaport, Small Time Crooks is the pitch-perfect comedy, and Woody Allen at his finest.

 

--Diner

Barry Levinson wrote a love letter to his hometown with Diner – a witty comedy set on New Year’s Eve 1959, the dawn of the new decade -- about a group of longtime friends whose lives intersect in Baltimore.

Starring the young Mickey Rourke, Tim Daly, Steve Guttenberg, Kevin Bacon, Daniel Stern, and Ellen Barkin – before each went on to greater fame – Diner weaves together the hilarious – and sometimes heartbreaking – story of each character as they grudgingly leave behind their youth and enter adulthood.

 

comedies

 

--Night on Earth

Jim Jarmusch is one of those quiet filmmakers who delivers astonishing films every few years. His best, in my humble opinion, is Night on Earth – with a fantastic theme song by Tom Waits – which tells the story of a handful of taxi drivers and their passengers around the world: from Los Angeles to New York to Paris to Rome to Helsinki.

Night on Earth is a riveting series of vignettes – but special kudos go to the hilarious New York and Rome segments, starring the great Giancarlo Esposito and Rosie Perez as the sassy Brooklynites who ride in German immigrant Armin Mueller-Stahl’s cab; and the Oscar-winning actor Roberto Benignini as the hapless Italian cabbie, who confesses his egregious sins to an ailing priest he picks up in his cab in Rome. 

 

--Annie Hall

Can any Best Comedy list really be complete without mentioning Annie Hall? A hilarious and touching love story – based loosely on the real-life relationship between its stars, Woody Allen and Diane Keaton – Annie Hall broke so many important barriers in filmmaking, and is considered one of Allen’s masterpieces.

The dynamic between Allen’s neurotic Alvy Singer and the sweet but dim Annie is seamless – and the dialogue and witty repartee are similar to watching the finals at Wimbledon – a never-ending volley of delightful, sharp quips.

 

comedies

 

--The Goodbye Girl

Of course, Neil Simon deserves a spot on my list, and one of the best comedies I have seen is The Goodbye Girl, a funny and charming movie, which earned an Oscar for Richard Dreyfuss, and nominations for Marsha Mason and Quinn Cummings. 

A down-and-out actor from Chicago (Dreyfuss) arrives in New York City for his big acting break, only to find that the apartment he thought he had sublet is still inhabited by his friend’s ex-girlfriend and daughter. Mayhem and an emotional tug-of-war ensue, as Dreyfuss and Mason duel over their awkward living situation, and surprise themselves as feelings develop.

 

--The Man Who Came to Dinner

See this film. It’s an oldie (from the 1940s) and darned funny. The irrepressible Monty Woolley stars as Sheridan Whitehouse, a rough and gruff – and strongly opinionated – radio personality who, as a result of an unexpected fall, becomes a very annoying houseguest at the home of a prominent family in Ohio, where he had planned a visit. With a young Bette Davis as his unusually patient assistant, Whitehouse offends all those who come in contact with him.

Based on the famous play by Moss Hart and George S. Kaufman, The Man Who Came to Dinner is a hilarious romp – and Woolley takes the cake as a master wit.

 

comedies

--Plaza Suite 
Yes, another Neil Simon play developed into one of my favorite comedies. The one and only Walter Matthau stars in all three skits, filmed at New York’s legendary Plaza Hotel. With his leading ladies in tow -- Maureen Stapleton, Barbara Harris, and Lee Grant – he stars as an adulterer; followed by a randy Hollywood producer; and finally, a New Jersey father whose bride-to-be daughter decides to lock herself in the Plaza Hotel bathroom on her wedding day.

Matthau is a comedy legend, so it’s no surprise that he can transform himself into three completely different characters and wow us every time. But special praise must also be heaped upon Stapleton, Harris, and Grant, his costars, who are the yin to his yang.

 

--Tampopo

Tampopo is without a doubt prominent Japanese filmmaker Juzo Itami’s comedic masterpiece, and a must-see for all film buffs. (Itami died quite tragically years after directing the film.)

The crux of the story centers around a truck driver and his relationship with Tampopo, the owner of a noodle shop, and their aspirations to turn Tampopo into a noodle-making machine.

Along the way – replete with unique and hilarious Japanese humor – viewers watch as the human race’s often bizarre – and eyebrow-raising -- relationships with, and love of, food unfold on screen in belly-aching comedic segments.

 

comedies

 

--Robert et Robert

Renowned French filmmaker Claude Lelouch makes astonishing films – and his A Man and a Woman catapulted him to international fame. In this sweet, witty, cinematically beautiful film from the ‘70s, two gentlemen, both called Robert – one a shy, quiet policeman-in-training; the other a cranky and anxious taxi driver, decide that they can best meet women by joining a computer dating agency. Needless to say, hilarity ensue.

Charles Denner and Jacques Villeret nail their performances with deadpan humor, and under Lelouch’s expert direction, the world of the Messieurs Robert comes alive in a fantastical and witty tour-de-force that catapults this film to cult classic status.

 

--Fast Times at Ridgemont High and Sixteen Candles

Both films played an important role in my youth: I would, and still watch, Fast Times at Ridgemont High and Sixteen Candles whenever possible with friends and family, and we all marvel at the superb scripts and characters – particularly the interactions between the perpetually stoned surfer Jeff Spicoli (Sean Penn in an unforgettable turn) and his frazzled teacher, Mr. Hand (the late, great Ray Walston) in Fast Times, and the hilarious friendship between Molly Ringwald’s and Anthony Michael Hall’s characters in Sixteen Candles. Directed by Amy Heckerling and John Hughes respectively, both films deftly capture the spirit of youth culture in America during the ‘80s – and all the silly mayhem and trials and tribulations that are part and parcel of being a teenager. 

 

comedies

 

--The Taming of the Shrew

I grew up having to study Shakespeare in school, and I am quite fond of the bard – particularly his comedic plays. And 1967’s The Taming of the Shrew is my favorite. In a cinematic coup, director Franco Zeffirelli landed Elizabeth Taylor and Richard Burton – Hollywood’s famous “it” couple at the time – to play the proud, headstrong, quick-tempered Katarina, who lives as she pleases and refuses to marry; and the strong-willed Petruchio as the man who is determined to marry her, becomes her husband, and eventually “tames” her. 

The chemistry between Taylor and Burton helps cement Katarina and Petruchio’s turbulent, unpredictable, and obstacle-ridden love story as one for the ages. 

Burton and Taylor deliver witty, smart lines, and with a renowned cast of Shakespearean-trained actors in tow (Cyril Cusack, Michael York et al.), this is a very funny and delightful movie that goes to show that, to quote another of the bard’s famous lines: “The course of true love never did run smooth.”

 

comedies

 

--The Ladykillers (1955)

The Ladykillers was also an honorable mention in my Best Films We Have Ever Seen list:

Do not watch the 2004 Coen brothers’ remake of this film – which is an unfortunate disservice to the its great comedic legacy. Instead, find the 1955 original directed by Alexander Mackendrick and produced by the famous Ealing Studios – starring some of Britain’s most notable talents: Alec Guinness, the young Peter Sellers, Herbert Lom, and Katie Johnson as the immortal Mrs. Wilberforce – better known as “Mrs. Lopsided.”

Guinness is the brains behind a gang of criminals – masquerading as musicians – who are plotting a robbery while renting rooms from Mrs. Lopsided. Their dreams of wealth quickly fall to pieces as the incorrigible Mrs. Lopsided catches on to their scheme and demands they return the money.

This is one of the most hilarious comedies I have ever seen: the cast, especially Guinness and Johnson are superb; the plot is fascinating; and the Oscar-nominated script, written by the immensely talented William Rose who would later win an Oscar for writing Guess Who’s Coming to Dinner – another all-time favorite film – is brilliant. If you want to spend an evening just laughing aloud, watch The Ladykillers.

 

comedies

 

--Forrest Hartman, Chief Film Critic:

 

--This is Spinal Tap

As a musician devoted enough to play weekend gigs, I am immediately drawn to any film that addresses the joy (and drama) of band life. No movie does this better than director Rob Reiner’s 1984 mockumentary about a hard rock group struggling to remain relevant in a fickle industry. Its satirical depictions of the larger-than-life personalities you find in music are spot on, and the picture hilariously riffs on the struggles every music group faces. The fact that writers/stars Christopher Guest, Michael McKean, and Harry Shearer actually play, allowing them to create a hilarious soundtrack, makes every scene feel authentic. On a scale of one to 10, this film goes to 11.   

 

--There’s Something About Mary

Just like filmmaking brothers Bobby and Peter Farrelly, Ben Stiller has a large repertoire containing hits and misses. For this picture, they combined talents, and it’s all hit. Stiller stars as Ted, a writer who has been kicking himself since missing out on a high school date with his dream girl, Mary (Cameron Diaz). Circumstances allow them to reconnect, but Mary is such a catch that Ted is competing with countless suitors. Hijinks and hilarity ensue.  

 

comedies

 

--The Wedding Singer

Adam Sandler, although ridiculously talented, is spotty. Some of his work (especially in dramatic turns) is brilliant. At other times, his antics seem forced, theatrical, and even annoying. He is at his best when restrained enough to focus his frenetic energy on building a well-rounded character. That is the case with his take on Robbie Hart, a wedding band singer who loses his spark after getting dumped. Julia Sullivan (Drew Barrymore) could be just the person to fix that, but she’s engaged to another man. There are plenty of comic moments as these two leads mingle, and Robbie’s spirited performance of the J. Geils hit Love Stinks is nearly worth the price of a rental.    

 

--Clerks 

Kevin Smith was a no-name when this smart, independent comedy stormed into theaters. Filmed on a $28,000 budget and featuring inexperienced screen actors, it relied on the charisma of the players involved and Smith’s impeccable writing and comic timing. Smith is witty, raunchy and – above all – passionate. That shows in this delightful comedy about two convenience store clerks navigating work, romance, and other trials life. Clerks is also noteworthy for introducing the world to Jay (Kevin Mewes) and Silent Bob (Smith), characters who would become pop culture icons worthy of their own films, cartoon series, and comic books. 

 

comedies

 

--Forgetting Sarah Marshall 

When Sarah Marshall was released, Jason Segel was already a star thanks to his starring role on the hit TV show How I Met Your Mother and his prior outing in Freaks and Geeks. This film demonstrated the depth of his talent, serving as an early indicator that his career would have legs. Segel, who stars, wrote the screenplay, and director Nicholas Stoller was the perfect director to execute his vision. The plot involves Peter Bretter (Segel) taking a Hawaiian vacation to forget about his ex (Kristen Bell). That becomes impossible when she shows up with a new boyfriend. Segel and Bell are great, as are Mila Kunis and Russel Brand in supporting roles.  

 

--Deadpool

Although not as traditional as previous picks, this action-comedy leans heavily toward laughs. In fact, many of the action sequences contain sight gags and comic riffing. This is consistent with the comic book presentation of Deadpool, and both Ryan Reynolds and director Tim Miller get credit for making an R-rated superhero flick into a blockbuster. Although Deadpool 2 is outstanding and Deadpool & Wolverine has good moments, it’s this first screen incarnation that made me a fan.    

 

comedies

 

--Confessions of a Dangerous Mind 

George Clooney’s debut as a director was among the best films of 2002, largely thanks to his excellent cast and darkly hilarious source material from gameshow host Chuck Barris. In his like-titled autobiography, Barris claimed he led a double life, working as a CIA hitman while simultaneously hosting The Dating Game TV show. The premise is nutty fun, and Sam Rockwell is brilliant as Barris. Add Drew Barrymore, Julia Roberts, and Clooney as costars, and you have dark comedy gold.  

 

--Office Space 

Surprisingly, office life continues to look much like it did a quarter century ago. Many folks still work in cubicles, answer to too many bosses, and get beaten down by poorly conceived corporate edicts. And, of course, we still have downsizing, although clever public relations professionals rebranded that as “rightsizing.” Office Space takes a shot at all of this by following the exploits of a lovable slacker named Peter (Ron Livingston) as he navigates a frustrating corporate landscape. This film is a classic because the sardonic wit of writer-director Mike Judge (Beavis and Butt-HeadKing of the Hill) still hits home. 

 

comedies

 

--Ferris Bueller’s Day Off 

I would lose my ’80s street cred if I created a comedy list excluding the late John Hughes. For many of my generation, Hughes was a cultural hero. He simply got us. As a director, he delivered not only Ferris Bueller’s Day Off but Sixteen CandlesThe Breakfast ClubWeird Science, and Planes, Trains and Automobiles. Look at his huge body of work as a writer and you can add more titles, including National Lampoon’s VacationSome Kind of Wonderful, and Home Alone. His is a tremendous catalog, but I think Bueller – about a charismatic high school senior (Matthew Broderick) who skips school for an epic adventure – will be remembered as his best.   

 

--Life Is Beautiful

When this film received seven Oscar nominations, including nods for best picture and best foreign film, it was widely promoted as a Holocaust comedy. Obviously, that designation seems oxymoronic, but it is oddly accurate. To be sure, writer-director Roberto Benigni’s masterpiece is more tragic than funny, but there is no ignoring his comic genius. The film tells the story of Guido (Benigni) and Dora (Nicoletta Braschi), a charming couple whose fairytale romance is derailed by the Nazis. Despite the horrifying reality, Guido uses his wit and charm to convince his young son that their internment is just a game. The film makes broad statements about love, dedication, and the bonds of family. It also may also make you cry, but Benigni delivers plenty of joy to counter the sadness. 

 

comedies

 

--School of Rock 

Long before Mike White created the HBO hit White Lotus, he wrote this wonderful film about Dewey Finn (Jack Black), a would-be rock star who cons his way into a substitute teaching job for which he isn’t qualified. Since all Finn wants is a paycheck, he skates through his days, largely ignoring the gifted students who want to learn something. Everything changes when Dewey discovers that many of them are excellent musicians. Suddenly inspired, he begins schooling them in the ways of rock ’n’ roll, while turning them into a darn good band. 

 

--His Girl Friday 

We can’t talk comedy without mentioning the screwball genre. Since this film was released in 1940, it lacks today’s progressive mindset. In fact, the story – about star reporter Hildy Johnson (Rosalind Russell) getting wooed by her editor/ex-husband Walter Burns (Cary Grant) -- can fairly be critiqued as sexist. But it was somewhat progressive in its day. Despite Hildy putting up with unseemly behavior, she’s the smartest person in every room, and she makes that clear with lightning-fast dialogue exchanges that always land her on top. Russell and Grant were true movie stars, and director Howard Hawks was an expert at pacing. If you aren’t familiar with this genre or cinematic era, add this one to your list. You may get hooked.

 

comedies

For Highbrow Magazine

Highbrow Magazine

Tags