Will Smith is one of the biggest movie stars in the world, but the movie he took over The Matrix is easily the biggest mistake in his career.

Will Smith is, to many, one of the last big movie stars in the world, a name that is known the world over and can drive audiences out to the movies. While his Academy Award win was overshadowed by the infamous Chris Rock slap, he still has many fans around the world. He is the star of beloved films like Men in Black, Independence Day, and The Pursuit of Happyness while also lending his image to IP-driven films like Suicide Squad and the 2019 Aladdin live-action remake. Fans eagerly await the release of Bad Boys Ride or Die, the fourth entry in the successful Bad Boys franchise, set for release this summer.

Despite a career of highs and lows, one film has certainly haunted Smith’s career. The 1999 action/sci-fi/comedy/western Wild Wild West. Adapted from the television show of the same name, the movie sees Smith play Jim West, a cowboy who teams up with inventor Artemus Gordon (Kevin Kline) to stop the Confederate solider veteran Dr. Arliss Loveless (Kenneth Branagh) from kidnapping the President of the United States in a giant robot spider. Originally anticipated to be one of the biggest hit movies of the summer of 1999, the movie became a box office flop and a critically mocked movie that even Smith’s own mother reportedly didn’t even like.

Will Smith Was a Fan of the Wild Wild Wild West Show

Wild Wild West originally began as a television show known as The Wild Wild West, which ran for four seasons from 1965 to 1969. Pitched as James Bond with horses, the following Secret Service agents, James West (Robert Conrad) and Artemus Gordon (Ross Martin) used a wide variety of high-tech gadgets for the time period to stop threats to America.

The feature film looked to act as a big-budget origin story for the setup of the television series. In 1992, Warner Bros. began developing the project as a feature film and eventually would sign on director Barry Sonnenfeld and star Will Smith in 1997, when Men in Black had become the biggest movie of that summer movie season.

Around this time, Smith was also offered the role of Neo in The Matrix, and at the time, Val Kilmer was considered for the role of Morpheus. Smith turned the part down as he did not quite get the script. Instead, he opted to make Wild Wild West as he was a fan of the television series. The Matrix would eventually see Keanu Reeves step into the role of Neo, with Laurence Fishburne cast as Morpheus.

The Matrix was released in theaters on March 31, 1999, three months before Wild Wild West, and would be regarded as not only one of the best films of that year but one of the most groundbreaking movies of all time. Meanwhile, Wild Wild West became one of the worst movies of 1999 and one of the worst movies in everyone’s career, a decision Smith would later regret.

What Went Wrong with Wild Wild West?

On the surface, Wild Wild West seemed destined to be a hit. In the 1990s, adaptations of popular television series from the 1950s and 1960s were all the rage, from box office smash hits like The Flinstones and Mission: Impossible to the Academy Award Best Picture nominee The Fugitive. For every flop like Lost in Space, others like George of the Jungle would go on to become cult classics.

It seemed a particularly profitable prospect for Warner Bros. as, in 1994, they successfully adapted the Western television series Maverick into a feature film that grossed $101 million at the domestic box office and earned positive notifications from critics and audiences. In fact, Maverick director Richard Donner and star Mel Gibson were initially developing Wild Wild West back in the 1990s before switching projects to another Western television series adaptation.

Meanwhile, Wild Wild West director Barry Sonnenfeld’s previous adaptation of a television show, The Addams Family, was a box office smash hit and combined that with Men in Black, a sci-fi comedy starring Will Smith released over the Fourth of July weekend, so too would Wild Wild West which was also a sci-fi (steampunk) comedy with Will Smith released over Fourth of July weekend.

Was the Robot Spider the Nail in the Coffin?

All the ingredients for a box office hit were there, but this was a case of something on paper that didn’t quite translate. One major factor working against the film was producer Jon Peters. Many have mocked the giant robot spider in the film’s third act, and this was a particular request from Peters as he had already tried to get a giant spider in both the canceled Superman Lives movie that Kevin Smith was hired to write and Tim Burton signed on to direct.

Neil Gaiman even said Peters wanted to have a giant spider in a film adaptation of Sandman that was attempted in the 1990s. After two failed attempts to get the giant spider in, Peters got his wish in a film whose budget ballooned and seemed to be bogged down in notes, trying to capture the formula of Men in Black and The Addams Family into one movie without trying to make Wild Wild West its own.

Wild Wild West Became a Box Office Bomb

Wild Wild West was released in theaters on Wednesday, June 30, 1999, to tie in with the upcoming Fourth of July holiday. Smith’s two previous movies, Independence Day and Men in Black, opened to massive box office numbers over that time frame in 1996 and 1997 and earned him the nickname “Mr. Fourth of July Weekend.” From its release to the holiday on Sunday, it grossed $40 million at the domestic box office and took the number one spot.

Unfortunately, though, it fell to second place the following week, and by the end of the month, it was out of the top 10. It closed its run with $113 million domestic against a reported budget of $170 million budget, making it a box office flop. Even worse, some reports suggest the movie costs up to $241 million, so even the total of $221 million worldwide doesn’t make up the difference.

Some theories suggest the movie was seen by fewer people than the box office would imply. The R-rated comedy South Park: Bigger, Longer, and Uncut was released the same day as Wild Wild West, and then the following week, American Pie was released in theaters and knocked Wild Wild West from the top spot. Many have speculated that younger moviegoers under the age of 17 likely purchased tickets for Wild Wild West and later snuck into R-rated features like South Park or American Pie.

The Aftermath of Wild Wild West

Wild Wild West being a box office flop, had major repercussions in the years that followed. One of the most immediate was the film The Iron Giant. Warner Bros. invested so heavily in Wild Wild West from a marketing standpoint that they paid little attention to The Iron Giant, only producing one promotional poster. The Iron Giant‘s positive test scores from test audiences took Warner Bros. by surprise, but it was too late to secure fast-food or cereal tie-ins like a traditional animated movie would have.

While Warner Bros. later invested heavily in promoting The Iron Giant home video release in theaters, the movie was a box office bomb. Today, The Iron Giant is considered one of the greatest animated movies of all time, while Warner Bros.’s big 1999 summer blockbuster Wild Wild West is not considered the best anything.