Summer of 1999: Six Underrated Movies from an Iconic Summer

1999 is considered by many to be one of the greatest movie years of all time and rightfully so. It was a legendary year filled with incredible movies from incredible filmmakers. Several great movies came out in 1999 from some of the greatest filmmakers to ever step behind the camera. We saw directors like David Fincher, David O. Russell, and the Wachowskis have breakout hits. We got films from established directors like Martin Scorsese, Spike Lee, Michael Mann, David Lynch, and Tim Burton. And we also saw the debut films from directors like Sam Mendes and Spike Jonez. It was one hell of a year.

The summer of 1999 was as epic as summers get for movies. The summer started with arguably the most anticipated movie of the last twenty-five years, Star Wars: Episode I – The Phantom Menace. While the film saw mixed reactions amongst critics and fans, it still ended up the highest-grossing movie of 1999. The summer also saw movie star vehicles like Big Daddy, Wild Wild West, and The General’s Daughter all make bank at the box office and saw huge hits like American Pie, The Blair Witch Project, and The Sixth Sense come out of nowhere and take the summer by storm. It was a special summer filled with so many movies that anyone could find a reason to go to the movies.

But with so many great and interesting movies and so many movies making money, some movies got lost by the wayside. Whether it was from poor critical reviews, unproven stars in the movie, the subject matter, or the film coming out the same weekend as one of the summer’s biggest hits, there were a few great movies that failed to make a spark with fans. Here are six under-seen and underrated gems from the summer of 1999. The films listed are films that underperformed critically, financially, or both but are really good films that I feel were misunderstood at the time or just didn’t have what it took to make a splash in such a loaded summer.

Bowfinger (Frank Oz)

Bowfinger is a great movie. It was great when it came out and it is great today. This Hollywood satire follows a desperate movie producer (Steve Martin) who tries to bag a major movie star (Eddie Murphy) for his next movie. When he fails to do so, he has the idea to secretly make an entire movie shooting around the movie star as he goes about his regular life.

Bowfinger made $66 million at the domestic box office, which is significantly more than any of the other films on this list. But, with a budget of $55 million, it’s hard to call the film a real success. It’s a smart, uproarious comedy featuring sensational performances from Martin and Murphy. Had the film been released earlier in the summer, I feel like audiences would have responded better to it and it would have had the legs to become a success. But being dumped in August as the summer was dwindling stopped Bowfinger’s chances of that success, even though it is arguably the best comedy to come out in the summer of 1999.

Dick (Andrew Flemming)

Andrew Flemming’s hilarious reimagining of the Nixon Watergate scandal finds two sweet but ditzy girls (Michelle Williams and Kirsten Dunst) who start working for President Richard Nixon (Dan Hedaya) but end up getting fired and become the legendary Deep Throat whistleblowers on the Watergate scandal.

Despite being well-reviewed by critics, Dick was a commercial flop. It came out the same weekend as M. Night Shyamalan’s The Sixth Sense, a surprise hit critically and financially that took cinemagoers by storm and was competing with other comedy films that were released around that time like American Pie, Big Daddy, and Runaway Bride. This is fun political satire and would make a very amusing double feature with All the President’s Men.

Drop Dead Gorgeous (Michael Patrick Jann)

Another 1999 Kirsten Dunst dud. This time, it was Michael Patrick Jann’s dark comedy about a beauty pageant in a small-town Minnesota that starts to turn deadly. The film stars Dunst, Allison Janney, Denise Richards, Ellen Barkin, and Brittany Murphy, and features the screen debut of Amy Adams.

Drop Dead Gorgeous is an absurd, quirky mockumentary reminiscent of Christopher Guest. The cast is firing on all cylinders, particularly Richards who gives the best performance of her career. The film is a heightened look at small-town America and the competitive spirit of beauty pageants while subverting the tropes of teen rom-coms that were dominating at the time. Audiences and critics in 1999 did not seem to agree, however, as the film only made $10 million at the box office and saw less-than-stellar reviews.

But despite its lack of success at the box office and with critics, Drop Dead Gorgeous has grown a cult following over the last 25 years as a Y2K camp classic.

Mystery Men (Ben Stiller)

When you look at Mystery Men’s cast, why it wasn’t a success is very confusing. It starred Ben Stiller, fresh off the success of There’s Something About Mary, Jeneane Garofolo, who was on the rise in the film and comedy world, William H. Macy, Greg Kinnear, and Geoffry Rush, all three were coming off recent Oscar nominations, Hank Azaria who was killing it on The Simpsons, Kel Mitchell who was a star on All That and Kenan & Kel, and former child icon Paul Ruebens. It was also an original and comedic take on the superhero genre and seemed ripe for

There were a few reasons why the film was not a success. The reviews of the film were mixed, with some critics liking its humor and characters while others dismissed it for not reaching the heights of a spoof comedy. Like Dick, it came out the same weekend as The Sixth Sense and there was no stopping that train. And the superhero genre was not nearly as big in 1999 as it is today. In the 90s, we maybe got one or two superhero movies every couple of years, unlike now where we get one or two almost every year.

Despite its box office woes (the film only made $29 million domestically on a $66 million budget), Mystery Men feels ahead of its time in mocking comic book movies and has enough comedy, action, and star power to be an entertaining and biting superhero satire.

Run Lola Run (Tom Tykwer)

A non-linear German thriller getting dropped between Tarzan and Big Daddy in one of the biggest summers of all time? It might sound strange, but that’s exactly when Tom Tykwer’s kinetic thriller was released in the U.S. This inventive movie shows Lola (an extraordinary Franka Potente) trying to get 100,000 deutch marks to her boyfriend so he can deliver it to the mob or else he will be killed. The film shows three different scenarios of Lola trying to get her boyfriend the money, each with slight changes that make the film gripping to watch.

Run Lola Run is a beloved work of world cinema and was snubbed of an Oscar nomination for Best Foreign Language film, but it is a perfect summer movie. It has energy, action, excitement, and an interesting lead, and will captivate you the entire time. For a foreign film that only played at 172 screens at its peak, Run Lola Run was very successful, grossing $7 million at the domestic box office and becoming a critical and art-house favorite.

Summer of Sam (Spike Lee)

Spike Lee had an interesting 1990s. He would make a sprawling epic like Malcolm X and then would make several music videos and then follow those up with smaller, more personal films like Get on the Bus or 4 Little Girls. He capped off the decade with Summer of Sam, a fictionalized account of the lives of a group of Italian Americans in the summer of 1977 as the Son of Sam serial killings are taking place.

Like a lot of Lee’s movies, Summer of Sam breaths and bleeds New York City. Lee’s film is a hot, sweaty, energetic look at an electrified city that was cast in paranoia, fear, and excitement as the city not only had a serial killer on the loose but had to deal with a major city-wide blackout and the Yankees making a legendary run. The film doesn’t solely focus on the killings but rather on the people living in the city and how they were affected by the killings and blackout while also dealing with their own issues like infidelity, trust, and scapegoating.

Summer of Sam is a fascinating film and one of the most underrated in the great director’s filmography. It’s a shame the film failed to take with audiences when it was released in July of 1999, but it has aged well and is worthy of a revisit.