Is Flirting With Disaster the most underrated comedy of the 1990s?

As far as the history of the movie goes, there’s perhaps none more fan-favorite than the 1990s. It was full of titles from every genre you can think of, from Westerns and war movies to slice of life and sci-fi movies. But of course there was also a slew of hilarious comedies starring the likes of Jim Carrey, Bill Murray, Eddie Murphy, Robin Williams and even more contemporary underrated guys like Chris Tucker.


But there were also filmmakers who stood out during the past decade by providing movie fans with well-crafted and side-splitting projects. I immediately think of the Coen Brothers, along with others such as Kevin Smith, The Farrelly Brothers, Harold Ramis and Wes Anderson. But as for the movie at hand – Flirt with disaster (1996) – the product was directed by David O. Russell. And while you may not know him by name, you will no doubt recognize the titles of his other legendary films.

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The career of David O. Russell

Jennifer Lawrence Bradley Cooper Silver Linings Playbook 2012 Weinstein Company
The Weinstein Company

Today, David O. Russell is one of the most acclaimed directors Hollywood has to offer thanks to projects like The fighter (2010), Silver Linings Playbook (2012), and American hustle (2013). Those three films amassed a total of twenty-five nominations at the Academy Awards in just four years. And while he’s gotten some criticism lately for the lackluster release of his latest project Amsterdam (2022), that can’t take away from the accolades garnered by those three films mentioned above.

But the early years of O. Russell’s career were just as well received by critics. He debuted with Hit the monkey (1994) before moving on to the movie at hand. And regarding his very first feature film, it was released with great success in the critical and commercial boards. With a 92% approval rating on the critical consensus website Rotten Tomatoes coupled with over $1 million accrued on a $200,000 budget, the numbers speak for themselves.

But it also holds up wonderfully today as a comedy in general – and it does Three kings (1999), the director’s third-ever feature film. A war movie with George Clooney, Ice Cube and Mark Wahlberg leading the cast, it really holds up as a hilarious romp from the film’s opening frame until the final shot rings out. And, frankly, many of O. Russell’s projects have been labeled underappreciated over the years, just like Hit the monkey And Three kings.

But not all – while Joy (2015) received considerable acclaim, Casual love (2016) was so horrible that O. Russell legitimately had his name removed from the project using a pseudonym: Stephen Greene. Then there is I like Huckabees (2004) with Dustin Hoffman, Jude Law and Jason Schwartzman. It doesn’t come close to the name value of other comedies of its era. But in the end, one David O. Russell movie has been so overlooked, it’s easily one of the most overlooked comedies of its decade.

Other underrated comedies from the ’90s

gross point blank cusack
Buena Vista Photos

Plenty of movies from this decade have comedic value despite not telling a groundbreaking story. Take, for example, most films from this period that featured Adam Sandler Happy Gilmore (1995) and The wedding singer (1998). But it’s hard to argue that critics were harsh when it came to movies like Bill Madison (1996) and The Water Boy (1998). Then there are movies like Big Daddy (1999), which received mediocre review scores and equally embarrassing cash at the worldwide box office.

The sports comedy Kingpin (1996) was also underrated, despite the fact that the Farrelly Brothers directed some pretty big names – Woody Harrelson and Bill Murray, for example. It has 49% on Rotten Tomatoes and made $32 million at the box office on a $25 million budget. Not the worst numbers, and this isn’t to say they should have been exponentially higher or anything like that. But there is undoubtedly an argument for this.

The same can be said Bow finger (1999), with Steve Martin and Eddie Murphy. It could be most easily overlooked from a more modern perspective, as it grossed big money in theaters and (arguably) even got better marks in terms of review scores. Then again, the public has seemingly forgotten about it over time.

There are also movies from this period that were critically acclaimed along with impressive box office numbers but still managed to slip under the contemporary radar. What about Bob? (1991), for example, along with Gross point blank (1997) and even Analyze this (1999). But in the end, one movie stood out as the most underrated comedy of the 1990s.

Related: Why Grosse Point Blank Is John Cusack’s Best Rom-Com

Why flirting with disaster stands out

Flirt with disaster
Miramax movies

As a writer-director, David O. Russell can be classified as an author. His scripts generally have a primary focus on character – their maturation process from point A to point B. In other words, how they grow as people, coupled with how they interact. Their dynamics, so to speak. It’s a lot to keep track of from a pure character development perspective, but O. Russell was more than up for the challenge: Flirt with disaster.

It stars Ben Stiller as Mel Coplin, a young and newfound father who, with the help of his wife, played by Patricia Arquette, sets out to find his birth parents. But things get really intriguing when Tina, an adoption agency worker, shows up. Played by Tea Leoni, she and Mel develop an affair that provides the film as a whole with its most meaningful source of conflict. At least, as far as emotional development is concerned.

On the outside, Mel is obsessed with finding his real parents to trace his family roots now that he is married and has a child of his own. But what he didn’t know he needed was a close partner to satisfy his true desires. The love triangle that ensued produced a truly palpable dynamic that blossomed into the film’s final frame.

And that is ultimately what stands out so prominently Flirt with disaster. The director closely adheres to the concept of character in general, their dynamics and developments both. Not only is this an entertaining love story that will often make you laugh – it’s also a great movie overall with a witty, well-structured script and deservedly impressive performances to boot. Critics no doubt recognized this over the past decade, and the movie doubled its $7 million budget. But these days, this David O. Russell comedy doesn’t come close to the love it deserves.

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