Will Smith is undisputedly the most successful rapper-turned-actor in history. From dramatic biopics to ambitious sci-fi thrillers to romantic comedies, there aren’t many roles the Fresh Prince hasn’t been willing to touch. Big Willie has made some great flicks along the way, as well as a few duds. With his much-anticipated Suicide Squad in theaters now, HipHopDX takes a look back at Smith’s filmography, ranking his movies from worst to best.*

(*Only films that prominently featured Smith were included)

23. The Legend Of Bagger Vance (2000)

Director: Robert Redford [Editor’s note: SMH]

In the year 2000, Will Smith + Matt Damon + inspiring sports movie = automatic success, right? This movie, ladies and gents, is proof that greatness doesn’t always come from a cookie-cutter formula. Will plays an angel golf caddy named Bagger Vance (yes, really) who is sent to help a war-torn Rannulph Junuh (Damon) get his groove back on the course. Bagger Vance attempts to evoke emotions with golf-as-life metaphors that are really just bad advice from a caddy (What if someone had told Tiger Woods “Don’t worry about hitting the ball or where it goes. Just swing the club, feel the club?” On second thought, maybe they did somewhere in 2010). Simply put, this is one so-called legend that should have never, ever been told.

22. Wild Wild West (1999)

Director: Barry Sonnenfeld

Wild Wild West was a flop critically and commercially, earning just $222 million worldwide against its ridiculous $170-million-for-western-budget. The plot was simplistic and the old western sets and costumes came off as cheesy. Will Smith and Kevin Kline teamed up to provide big names but basically disappointed while exchanging jokes and attempting to stop Dr. Loveless from killing the president. Beyond the occasional TBS re-airing it doesn’t offer much in the way of a legacy outside of quirky robotic sequence and Smith recently pinpointed the flick as his worst movie to date. The only reason we’re not agreeing with him is Selma Hayek.

21. After Earth (2013)

Director: M. Night Shyamalan

Like father, like son? Not exactly. Will and his youngest offspring, Jaden Smith, did the family name justice in The Pursuit of Happyness but when Jaden was given more center stage to work with, the end result wasn’t as magical. Comparisons to …Happyness aside, Jaden just didn’t have his father’s renown big-screen presence nor the acting chops. It’s not all the youngin’s fault, though. With the exception of a few scenes, After Earth fails to match its CGI spectacle with a compelling plotline. And what was up with those accents?

where the day takes you poster

20. Where The Day Takes You (1992)

Director: Marc Rocco

In his film debut, a 23-year-old Smith found himself cast as a worldly bum with no legs as he was thrust into the type of early 90s drama that will forever be devoid of any cultural significance. The role showcased talent and diversity but ultimately was for naught. Smith wasn’t the only star (current and eventual) that raked up a forgettable project on the résumé. WTDTY also boasted the likes of Christian Slater, David Arquette, Sean Astin, Ricki Lake, Balthazar Getty and Lara Flynn Boyle.

19. Focus (2015)

Director: Glenn Ficarra & John Requa

For a romantic thriller that started off interestingly enough, it was pretty ironic that a movie named Focus lost all sight of that when the time came for the ending credits begin to roll. Smith plays Nicky, a con artist who takes on a protégé, Jess (Margot Robbie). The pair immediately develops chemistry, and one could argue this movie is worth it for the football game gambling scene alone. Yet, as the film becomes less intense and more, well, “focused” on a romance between Robbie and Smith, it stretches its purpose a bit too thin and never realizes its full potential.

will smith six degrees of separation

18. Six Degrees Of Separation (1993)

Director: Fred Schepisi

From an overall standpoint, Six Degrees of Separation isn’t a remarkable piece in terms of visuals, backdrops, fluidity or even overall dialogue but it does possess several attributes that contain noteworthy glimpses into everyday society (social status, education, naivety, racism). Based on the Pulitzer Prize-nominated play of the same name, the film is ultimately remembered for Smith’s character being gay, which showed acting range and the fact he was never out to let his Hip Hop status be refurbished for movie roles.

17. Concussion (2015)

Director: Peter Landesman

Will does a fine job as Dr. Bennett Amalu (just ask a bias-free Jada Pinkett Smith!) whose research on brain trauma led to a public relations nightmare for the NFL. However, in the film’s aim to deliver Amalu’s findings to the masses, it ignored key aspects that also could have contributed to the mental problems his subjects faced (i.e., steroids). The movie also ends on a decidedly anti-football note, ignoring the fact that steps have been taken to make the game safer. While Concussion aims to “tell the truth,” it only gives us part of the story.

16. Shark Tale (2004)

Director: Vicky Jenson, Bibo Bergeron and Rob Letterman

Robert De Niro, Martin Scorsese, Jack Black, Angelina Jolie, Renee Zellweger, and, of course, Will Smith. How can you go wrong with that lineup? Here’s how: this animated tale chronicles a whale-cleaning fish, Oscar (Smith) who gains fame when he tricks people into thinking he bravely killed a shark, Lenny (Black). The charade teams up Smith and Black, which might seem a winning combo, but this flick lacks both Smith’s charm and Black’s hilarity. There are a few strong jokes here and there, but they were better suited for the adults ushering their children to theaters opposed to the kids themselves.

15. Hancock (2008)

Director: Peter Berg

Before he was a supervillain in Suicide Squad, Big Will was a superhero in Hancock. Sort of. Will’s version of a superhero is a drunken, get-off-my-lawn sort of guy who does as much collateral damage as he does good. He enlists Ray Embrey (Jason Bateman) for a PR job, but when Hancock meets his publicist’s wife, Mary (Charlize Theron), that’s when things get interesting, and not in the way you might expect. Unfortunately, that’s when this movie goes all over the map. Still, it remains fairly enjoyable, and it’s nice to see Will pull off a role that’s anti-charming. Call him “asshole” one more time…

14. Seven Pounds (2008)

Director: Gabriele Muccino

This heartbreaking film does as good a job of displaying Will’s range as any in his catalog, although the script doesn’t offer much believability. A tragic accident leaves Tim Thomas (Smith) guilt-ridden and going to extreme measures to atone. If you’re not stung by the bittersweet ending, then you should at least take away this from Seven Pounds: don’t text and drive.

13. Made In America (1993)

Director: Richard Benjamin

This oft-forgotten race relations comedy still can be recorded as a massive success for a number of reasons. For one, it made money (nearly $105 million worldwide when it was all said and done) which in turn, propelled Smith to secure more roles leading up to his Independence Day blockbuster. It also furthered the career of Nia Long, one of the most sought (and lusted) after actresses in the past 20 years. At the time, both Whoopi Goldberg and Ted Danson were considered A-listers as well, so all the parts just clicked, even if the film is rarely mentioned amongst any of the stars’ favored movie roles.

12. I, Robot (2004)

Director: Alex Proyas

Will Smith is amongst the best actors for an action film of all time and I, Robot provided a great canvass for him to run, jump and even do some allegorical exploration. (Sounds like a Mario Brother, right?) The film borrows very loosely from the short stories of Isaac Asimov and serves as an heir to the Terminator series. The movie finds police officer Del Spooner (Smith) skeptical of the robots that have come to live amongst humans in a futuristic world. Spooner, of course, ends up being right and having to fight back against the machines, providing for strong action sequences and shimmering special effects.

11. Men In Black II (2002)

Director: Barry Sonnenfeld

MIB II was nowhere near as charming as its predecessor, and not as creative as MIB III. However, Smith’s back-and-forth with Tommy Lee Jones keeps things funny and fresh throughout this sci-fi flick, as Will’s Agent J has to bring Jones’ neuralized Agent K back into the fold for a problem only the latter can solve. For Hip Hop heads everywhere, the beatbox scene between Smith and alien Biz Markie remains one of the best cameos of the like. The same can’t be said for Michael Jackson’s guest spot. R.I.P. but WTF?

10. Men In Black 3 (2012)

Director: Barry Sonnenfeld

Who said delayed third installments have to suck? This particular Men in Black come back with a fresh twist: Smith’s Agent J has to go back and time and team up with a young Agent K (Josh Brolin, who gets Tommy Lee Jones’ mannerisms down pat) in order to stop a catastrophe from happening. MIB³ is funny, action-packed and even manages to add a sprinkle of sentiment. Not bad for a movie No. 3.

9. Bad Boys (1995)

Director: Michael Bay

All Will Smith movies pre-Independence Day never were revisited and given a praiseworthy analysis of the Fresh Prince’s versatility on screen. The first installment of Bad Boys — which is also virtually the first Miami Vice movie — serves as a prime example as Smith’s Mike Laaarry (Lowery) character juggles the traits of a ladies’ man, LAPD marksman (in a good way; as in actually shooting actual bad guys) and invincible bodyguard for an unassumingly sexy witness to her friend’s murder (Téa Leoni).

8. Enemy Of The State (1998)

Director: Tony Scott

This pre-9/11 thriller was ahead of its time when it comes to the ‘ol they’re-bugging-our-milk-jugs rhetoric and overall concerns with homeland security. Will plays an attorney suffering from the worst case of wrong-place-wrong-time, on the run from Big Brother with a conspiracy-crazed “Brill” (Gene Hackman). Smith had been better, but he had never been this thrilling.

7. Hitch (2005)

Director: Andy Tennant

Will was born for the role of the love doctor, Alex “Hitch” Hitchens, who tries to help the hapless Albert (Kevin James) get the girl of his dreams, while courting the stunning journalist Sara (Eva Mendes). As things complicate with Sara and progress with Albert and his dream girl, it’s not as clear as to who’s helping whom. Hitch is funny, but its biggest accomplishment is that it remains cool while promoting a “be yourself” sentiment.

6. I Am Legend (2007)

Director: Francis Lawrence

With the most daring performance of his life, Will Smith shines in I Am Legend. He spends most of his screen time alone — save for his loyal dog Samantha — as Lieutenant Doctor Robert Neville. The intricate plot alludes to a cure for cancer gone wrong that leads to the dystopian New York City Neville inhabits, perpetually searching and reaching out for other humans who have not been turned into the vampiric monsters he evades as a result of the bad drugs. Smith carries the film for 100 minutes in a movie that is not only exciting but a thought-provoking distinction in the overflooded world of disaster flicks.

5. Men In Black (1997)

Director: Barry Sonnenfeld

Aside from being a great flick, Men in Black was one of two movies (along with Independence Day) that legitimized Big Willie Style as a movie star. At this time studios realized that the Fresh Prince was a sure thing to make good films and more importantly make money. Smith portrays Agent J, an NYPD officer who is recruited by Agent K (Tommy Lee Jones) into a top-secret organization of earth defenders called Men in Black. Naturally, it’s not long before they have to save the world. Watching Smith and Tommy Lee Jones fight aliens across Manhattan and Queens is mass appeal entertainment at its finest. The film has entered the territory of iconic nearly two decades since its release which inevitably has led to inferior, but still enjoyable, sequels.

4. Bad Boys II (2003)

Director: Michael Bay

How did Michael Bay, Will Smith and Martin Lawrence follow up their 1995 cult classic? They waited eight years and jacked up the budget by a cool $111 Million. (Don’t worry, they definitely made it back and then some.) The original Bad Boys was an intense buddy-cop comedy with one-liners for everybody, but Bad Boys II was grandiose in scale and satisfyingly obnoxious in its over-the-top nature. Marcus (Martin Lawrence) and Mike (Will Smith) work to topple Johnny Tapia (Jordi Mollà) and his Miami ecstasy empire, but things take a turn for the worse when Marcus’ special agent (and inexplicably attractive) sister Syd (Gabrielle Union) is kidnapped by Tapia. There are more than a few chase/shootout scenes, but the denouement has to be Mike and Marcus driving their hummer through a Cuban shantytown, destroying everything in their path. It may not be rich in substance, but the sheer entertainment value absolutely cannot be denied.

3. The Pursuit Of Happyness (2006)

Director: Gabriele Muccino

The plot of Pursuit of Happyness was, at the time, considered outside of Will Smith’s wheelhouse and showcases his acting range. Skepticism preceded the film’s first announcement as to whether an action star could deliver a performance meant to tug at heartstrings. Will silenced his critics, even bringing his then six-year-old son Jaden along to play his character Chris Gardner’s son in the movie. Happyness is an adaptation of Gardner’s memoir, finding him working as hard as possible to escape poverty and the difficulties of class mobility for his own gain, and more importantly the betterment of his son’s life. It delivered Will his second Oscar nomination for Best Actor in a Leading Role.

2. Independence Day (1996)

Director: Roland Emmerich

The mid-1990s were the peak of Will’s obsession with aliens. Just one year prior to the release of Men In Black, Dean Devlin and Roland Emmerich’s Independence Day was THE supernatural box office dynamite. Will’s character, Captain Steven Hiller was incredibly endearing, and the film tastefully exercised its budget with technological advancements and cutting edge CGI effects. Oh, and the story itself was actually good, too. Whether it was Will and Jeff Goldblum trading friendly barbs, Mary McDonnell and Vivica A. Fox having a heart-to-heart, or just the presences of Randy Quaid and Robert Loggia, Independence Day achieved staying power with its cast of characters and unique storyline, that at the time was a far cry from a handful of alien film predecessors.

1. Ali (2001)

Director: Michael Mann

“Rumble, young man, rumble.” This earned Big Willie his first Oscar nomination for Best Actor in a Leading Role. Ironically, Will initially balked at playing Muhammad Ali, because he didn’t think he would be right for the part. It’s a good thing for us he changed his mind. That Louisville drawl, those classic Ali expressions and the depth he brought were perfect for the part. The film digs deep into the late American icon’s life as he wins his first Heavyweight boxing title, loses it and his boxing license for refusing entry into the military, wins his license back in the Supreme Court, and then beats George Foreman in the “Rumble in the Jungle.” Smith’s acting, stunning turns by Jon Voight (as Howard Cosell) and Jamie Foxx (as Drew “Bundini” Brown), as well as director Michael Mann’s vision of the turbulent times, make Ali a knockout and the best film he’s ever done.

Written by Jason Bischoff, Aaron Mckrell, Ural Garrett and Trent Clark