In 1998, Hollywood’s summer box office king, Will Smith, was in the middle of one of the most impressive runs in movie history. From 1995 to 2008, the artist also known as the Fresh Prince amassed well over $5 billion in ticket sales, propelled by an at times seemingly effortless genre-hopping range of films. It seemed like Smith could do it all: an action-rich buddy comedy (1995’s Bad Boys); an alien invasion flick (1996’s Independence Day); an over-the-top sci-fi romp (1997’s Men in Black); a conspiratorial political thriller (1999’s Enemy of the State); and Oscar-nominated biopics (2001’s Ali and 2006’s The Pursuit of Happyness). He also stuck the landing with a futuristic mortality tale (2004’s I Robot); an animated underwater adventure (2004’s Shark’s Tale); a slapstick rom-com (2005’s Hitch); a post-apocalyptic battle for the survival of the human race (2007’s I Am Legend); and a bold, risk-taking superhero flick for adults (2008’s Hancock).

“I found myself promoting something because I wanted to win versus promoting something because I believed in it.” – Will Smith

Which is why the Philadelphia-born hip-hop and movie icon’s steampunk western comedy, Wild Wild West (1999), is such a fascinating aberration. For starters, the full-blown popcorn disaster—which featured an at the time on-fire Smith as U.S. Army Captain James West, who, alongside Marshal Artemus Gordon (Kevin Kline), is tasked with hunting down Confederate war criminal General “Bloodbath” McGrath, and eventual big baddie Dr. Arliss Loveless—ranks as the superstar’s most infamous flop. 

With its eye-popping $170 million budget and paltry $222 million return, Wild Wild West, loosely based on the 1960s television series, has been elevated to epic bomb status; a cinematic monstrosity so over the top that it has now become the stuff of Tinsel Town legend. When the Golden Raspberry Awards, which recognizes the most embarrassing performances in the film world, named that movie Worst Picture in 2000, Wild Wild West’s original creator, Michael Garrison, accepted the dubious Razzies trophy (it won five out of nine awards for that year) with plenty of side-eye for the big screen version. Indeed, Wild Wild West was universally dragged by bleeding hearts, right-wing zealots, independents, babies, dogs, cats, rats, insects and just about every sentient being. 

But no one brought more contemptible rebuke than late Pulitzer Prize film critic Roger Ebert. “Wild Wild West is a comedy dead zone,” he bristled. “You stare in disbelief as scenes flop and die. The movie is all concept and no content; the elaborate special effects are like watching money burn on the screen.” Then there’s this gut-punch of a line: “There are moments when all artifice fails, and you realize you are regarding desperate actors, trapped on the screen, fully aware they've been left hanging out to dry.” Ouch.

And it gets worse. Wild Wild West’s flat jokes not only wasted the sizable talents of Will Smith and Academy Award winner Kline, it fumbled the esteemed presence of five-time Oscar-nominee and two-time Emmy winner Kenneth Branagh (Dr. Loveless) and future Frida actress and all-around powerhouse Salma Hayek (Rita Escobar). Oh, yeah. Smith actually turned down a headlining role in the landmark, game-changing The Matrix film series to star in Wild Wild West. Like we said. Pretty bad. 

Nearly 20 years later, Smith agreed with Ebert’s assessment of a project that he called his personal low point. “I had so much success that I started to taste global blood, and my focus shifted from my artistry to winning,” he recalled of his fateful decision to jump on board the Barry Sonnenfield-directed movie to the Hollywood Reporter during a 2016 interview. “I wanted to win and be the biggest movie star, and what happened was there was a lag — around Wild Wild West time — I found myself promoting something because I wanted to win versus promoting something because I believed in it.”

A philosophical Smith continued: “Back in the '80s and '90s you had a piece of crap movie you put a trailer with a lot of explosions and it was Wednesday before people knew your movie was shit,” Smith said. “But now what happens is 10 minutes into the movie, people are tweeting ‘This is shit, go see Vin Diesel.'”

There’s a lot not to like about Wild Wild West. It’s rarely funny; the characters are beyond formulaic; women are often used as props (Garcelle Beauvais deserved better); and an obscene amount of CGI, which includes a gaudy, giant mechanical spider, was merely paper over obnoxious dreck. 

Today, however, Will Smith is having the last laugh. The former box office champ has reinvented himself as America’s favorite dad; a beloved social media figure who has mastered the art of YouTube and Instagram, leaving his peers in the dust. And he’s still pretty good at the movie thing, as his much-praised turn as the genie in the live-action remake of Aladdin has taken in a remarkable $727,009,860 globally.  

But there is still something intriguing about the legacy of Wild Wild West: Race. As a Black man, Will Smith playing a cocky, brilliant, wise-cracking law and order gun slinger kicking ass just four years after the Civil War was pretty bold. There is a certain “woke” element to Wild Wild West, albeit rushed and at times historically laughable. Jim West doesn’t merely take on the assignment directed to him by President Ulysses S. Grant out of duty for country. He does so knowing that nasty baddie McGrath massacred an entire settlement called New Liberty, where many former slaves lived, including West’s parents. 

Sure, it’s wildly absurd to see Smith’s character make it out alive from a masquerade party packed with white Southerners—complete with the evil (and brazenly racist) Dr. Loveless literally exploding out of a large papier-mâché head of President Abraham Lincoln. “Looks like we need to teach y’all a little lesson on how to behave in a polite society,” says a man dressed as George Washington as a crowd drags West out to be lynched after he mistakenly touches a white woman’s breasts who he believes to be his partner in disguise. 

“Never drum on a white lady’s boobies at a big redneck dance… Sure am glad we got that cleared up,” snaps back a deadpan West. 

Of course, it should be noted that in real life Jim West wouldn’t even have had the chance to respond before meeting what would have been a horrific death; the sort of unspeakable, cruel murder at the hands of the kind of sickeningly hateful white racist mob that, according to the Equal Justice Initiative, took the lives of more than 4,084 African-Americans between 1877 to 1950. 

Wild Wild West essentially works as an early cartoon version of Quentin Tarantino’s bloody 2012 slavery revenge fantasy, Django Unchained, a film role Smith would ironically turn down. After several meetings with the maverick visionary behind such classics as Reservoir Dogs (1992), Pulp Fiction (1994), Kill Bill Volume 1 and 2 (2003, 2004) and The Hateful Eight (2015), the two disagreed on the underlining theme of the Oscar-winning movie.

"I wanted to make that movie so badly, but I felt the only way was, it had to be a love story, not a vengeance story," Smith explained during The Hollywood Reporter's annual Actor Roundtable in 2015. "Violence begets violence. I just couldn't connect to violence being the answer. Love had to be the answer." 

Smith’s Jim West is certainly no Django Freeman, played with all-out ferocity and powerful resolve by Jamie Foxx. Maybe it was a lack of a true love interest in Wild Wild West that played a role in the actor walking away from such a voluptuous comeback role. Still, Wild Wild West has one redeeming quality. Smith oftentimes gets the upper hand over an army of supposedly superior white men. While that's not quite enough to endure Big Willie butchering a rehashed take of Kool Moe Dee’s otherwise classic 1987 single “Wild Wild West,” at least you don’t have to envision Tarantino gleefully mouthing the N-word.        

For all its flaws, Wild Wild West lives on in a world that continues to blur the lines between principal and pastiche. Social media talent-turned-rapper Lil Nas X has parlayed the Black cowboy aesthetic, and a little bit of resistance from the establishment, into a runaway hit in “Old Town Road.” The anti-entertainer turned a snub from Billboard and country music radio into a chart-topping remix with Billie Ray Cyrus. Ever the good sport, Will Smith dubbed over footage from Wild Wild West with the song in a perfect homage to the “Yee Haw Agenda,” as it has been dubbed.

“Y’all Call me when you’re ready to shoot the video @lilnasx @billyraycyrus,” Smith wrote in the caption. Just leave the giant mechanical spiders out of it.