Will Smith the rapper – Top 10

Will Smith

Will Smith gurning

As Will Smith threatens to return to music, Getintothis’ Shaun Ponsonby looks through his back catalog with an abundance of “woos”, “hahas”, “what whats?”, “uhhs” and lots of gurning.

I think we can safely say, without hyperbole, that Willard Carroll Smith, Jr is the single most important human being of the late 20th Century. Hailing from West Philadelphia, born and raised, on the playground is where he spent most of his days, until he met DJ Jazzy Jeff at a house party.

Jeff was performing and his hype man was nowhere to be seen, so the teenage Smith filled in. They had such a good time that Jeff was apparently disappointed when his actual hype man finally showed up.

Given Smith’s resulting success as an actor – and one of Hollywood’s most bankable stars, or at least he was before After Earth – his rap career has largely been forgotten, but he was probably more important than he is given credit for. At a time when hip hop was seen as genuinely dangerous and threatening, DJ Jazzy Jeff & The Fresh Prince were frothy, funny and poppy. None of that militant Public Enemy shenanigans, or those gritty N.W.A. urban realities, and white America happily welcomed the pre-Rizzle Kicks onto their television screens and parents didn’t mind their kids listening to songs about not liking the clothes your mum picks out for you.

So, yeah, corny and cartoonish, but thanks to the turntablism of DJ Jazzy Jeff, they often managed to avoid falling into the trap that MC Hammer and Vanilla Ice found themselves in. Perhaps due to his association with the pop rap of DJ Jazzy Jeff & the Fresh Prince (and his role in The Fresh Prince of Bel Air), Jeff might be a little overlooked by the mainstream, but is widely regarded to be a pioneer of scratching.

Following Smith’s foray into movies, The Fresh Prince began releasing solo albums under his own name (let’s call this the “Big Willie” era), often as commercial tie-ins with his movies, but just as often not.

Where Will Smith fits in pantheon of hip hop when all is said and done is debatable, especially now that he seems to be sending his awful kids out to do his dirty work for him. But recently both Smith and Jazzy have been talking about a reunion tour and new material. Smith has been showing up and rapping on TV once in a while (most recently over the last few weeks on The Late Show with Stephen Colbert and at an event promoting his new movie Suicide Squad). It is hard to make this work when one of the duo is one of the planet’s biggest movie stars.

However should the tour happen in this time of 90s nostalgia, Willennials will fill the world’s arenas and insist on gettin’ jiggy wit it, with an abundance of the “woos“, “hahas“, “what whats?” and “uhhs” with which Smith litters every single track he has ever recorded.

Could Will Smith actually be the greatest rapper of all time?


Or could he be?

No, he couldn’t.

But could he really?

Not even ironically.

But he is entertaining all the same.

When this writer was talking to some whippersnappers in a college course I was teaching last year, I found out that these kids had no idea that Smith was a rapper before he was a movie star. So we decided awareness needed to be spread of one of the most deliciously cornball acts of all time.

We give you the Top 10 Will Smith and DJ Jazzy Jeff & The Fresh Prince.

If you like lists of things, you will love our archive of lists of things. Why not read them while you can?

  1. Boom! Shake The Room [DJ Jazzy Jeff & The Fresh Prince, 1993]

Hip-hop moved fast in the early 90s. Like, really fast. By now the golden age acts such as Public Enemy, Run DMC, De La Soul et al were starting to look a little old hat next to the onslaught of Gangsta Rap and the brutal urban realities of N.W.A., Wu Tang Clan, Biggie and 2Pac, so you start to find a lot of them trying to keep up in their own way. Run DMC made the almost baffling Down With The King album, and even the seminal pop rapper MC Hammer came out with the video for Pumps and a Bump (we implore you to watch that).

DJ Jazzy Jeff & The Fresh Prince responded with Boom! Shake The Room, a UK #1 no doubt propelled by the success of The Fresh Prince of Bel Air TV show.  What’s striking now is how unconvincing the whole thing is. Like, Will, you’re not gangsta. You’re the little rascal who makes cheeky fat jokes at Uncle Phil. The worst thing anyone has ever said about you is that Men In Black II was a bad movie. Just, no.

In particular, the line “Many have died trying to stop my show” sticks out. That’s a lie, isn’t it, Will? Just admit it, we won’t hold it against you. We know full well that nobody has ever lost their lives trying to stop DJ Jazzy Jeff & The Fresh Prince performing. What did you do? Gurn them to death?

Still, at least its fun.

  1. Will 2K [Will Smith Feat. K-Ci]

In 1982, Prince released the song 1999. In the 17 years leading up to that fabled year, it gradually became the anthem for the new Millennium. Fast forward to the event itself, and Will Smith released Will 2K, in which he basically took ownership of the new Millennium – or rather WILLennium, as he called it by cleverly turning a consonant upside down.

It was released just two months before the end of the year 1999. We don’t know how many of you remember the crushing disappointment of the turn of the Mill/Willennium, but the most exciting thing that happened was that everyone figured out what horseshit the Mill/Willennium Bug turned out to be. After all the build-up, it proved to be a let-down of gigantic proportions, and everyone went back to their crappy lives, with the added insult of a banging hangover.

So, in retrospect, this was never going to be a classic, was it? It’s built on a sample of The Clash’s Rock The Casbah, with the so-simple-it’s-Shakespeare re-write “Rock the dancefloor”. We assume people had thought to do this before, but rejected it for being obvious and hokey.

At the end of the day, though, it is a worthy inclusion and we need to honour Will Smith’s claim of ownership to the new Mill/Willennium, purely because nobody else thought to do it.

  1. Brand New Funk [DJ Jazzy Jeff & The Fresh Prince, 1987]

He’s The DJ, I’m The Rapper was DJ Jazzy Jeff & The Fresh Prince’s most successful album, and the first rap LP to win a Grammy for lead single Parents Just Don’t Understand. Although that lead single and Nightmare On My Street painted wholly a cartoonish image of the duo, the reality is a little more interesting, thanks in no small part to Jazzy Jeff, undoubtedly one of the turntable pioneers. Smith (as The Fresh Prince), in contrast, is the reason for the silliness, but at the same time his persona was the appeal of the duo in the first place.

Brand New Funk is probably the best example of Jeff’s handy work matching Smith’s chirpy MC’ing without it going too far into caricature. It’s all still a little naïve, but the humour and youthful exuberance haven’t diminished over the years, and it is an interesting snapshot of crossover hip hop in the late 80s.

  1. Switch [Will Smith, 2005]

As it stands, Smith’s most recent hit. By this point, he was an actor who occasionally rapped more than anything else, but this is a song we would say is actually really good without having to add the word “ironically” anywhere in the sentence. Most of the appeal of his back catalogue right now stems from nostalgia, but this one stands up. It shows a slightly more mature Will, but not one that has forgotten how to have fun. A deserved Top 10 on both sides of the Atlantic, that has sadly gone a little forgotten.

Despite it coming out the same year as his similarly titled movie Hitch, this is surprisingly not a tie-in to that film that we barely remember.

  1. Miami [Will Smith, 1998]

You could probably refer to this as Summertime II. Based on a sample of The WhispersAnd The Beat Goes On, it’s a pop-rap summertime jam that is ultimately harmless and will challenge you about as much as Ant & Dec, but that isn’t it’s intention, so why expect it to?

Lyrically, though, it appears to be a celebration of the multiculturalism of Miami, Florida, making it more than the party jam that it first appears to be.

The video is classic 90s, with Will getting a plane from Philadelphia to Miami and treating us to several costume changes. Some of these make sense, such as changing from black clothes to a white vest in the blazing sun. Others don’t, such as the fact that he wears trousers in the daytime and shorts in the nighttime. What kind of philistine are you, Smith?

  1. Men In Black [Will Smith, 1997]

The mid-90s were dark days for hip-hop. As we all know, the rise of the rivalry between the East and West coasts had devastating consequences, with the murder of 2Pac and Notorious B.I.G. You could argue that hip-hop had gone pretty damn dark, and the people couldn’t take it much longer. Balance was sorely needed.

Enter Will Smith’s solo comeback, with his new album featuring no swearing and a lead single that ties in with his new blockbuster! Yaaaaay!

This is one of the cheesiest things you could possibly imagine and nothing more than an advert for the movie. We can’t picture anything like this happening now. Imagine a single from Batman v Superman: Dawn of Justice that is actually directly about the movie. A song that actually talks specifically about the rivarly between Batman and Superman and the plot of the film.

The weird thing is, it works. In fact, it really works, fitting the movie perfectly and being a fun single in the process. Like the characters portrayed in the movie, the song is almost cold and unfeeling, so even if it is a glorified advert then some actual effort went into it.

At the time, it was the latest in a long, proud tradition of Will Smith tying in hits from his movies and TV projects, which began with The Fresh Prince of Bel Air, and continued with…

  1. Wild Wild West [Will Smith Feat. Dru Hill & Kool Moe Dee, 1999]

In truth, this has absolutely nothing to do with the movie it comes from. A western with a hip hop theme tune based on a Stevie Wonder sample? Yeah, as a movie tie-in, it doesn’t work anywhere near as well as well as Men In Black.

The movie sucked too. Apparently, Smith opted for Wild Wild West over The Matrix, which deprived the world of his inevitable soundtrack song for the latter. Imagine it over a sample of Boogie Wonderland or something;

Woo! It’s a simulated reality, haha!
Uhh, is it real or fantasy?
Whaaat? Whaaat? Big Will! Haha!

And the video would have been glorious. Imagine Will dancing with a gang of Agent Smiths, and a lengthy, plot-driven mid-section where everything slows down into bullet time. What could Buzzfeed have done with that in their innocuous bollocks of a 90s nostalgia-based listicles? The possibilities are endless.

Anyhow, Wild Wild West is much “bigger” than Men In Black. It clearly had more money to throw around (that the film didn’t recoup) and fully engages with its sheer ridiculousness, so it’s hard to fault it. Frankly it is a much more enjoyable listen than its predecessor. But, then, given than it is based on Stevie Wonder’s I Wish, this is hardly surprising. We’re pretty sure that is one song that is impossible to mess up.

  1. Gettin’ Jiggy Wit It [Will Smith, 1998]

The biggest non-movie song from his Big Willie Style album – his debut sans DJ Jazzy Jeff (in name, he’s on the album) – this almost sums up Smith’s appeal. Cool and laid back, but just goofy enough that you could imagine hanging out with him. Interestingly, Smith has said that the song came out of his association of the term “jiggy” with the racial slur “jigaboo“, and attempted to turn an offensive terminology into a racially empowering one. Bet you never considered that!

There have been rumours abound since the song’s released that the track was actually ghostwritten by Nas, but Nas has denied this, save for a line or two that he may have pitched in the studio as he was visiting Smith as the track was recorded.

Pitchfork named this one of the 7 worst #1 hits of the 90s. Seeing as Pitchfork is often the go-to place for snobs and people with no sense of humour about music, this writer would take that as a compliment (N.B. this does not reflect the view of the entire writing staff at Getintothis, many of whom love Pitchfork).

  1. Yo Home To Bel-Air [DJ Jazzy Jeff & The Fresh Prince, 1990]

We are pretty sure that there are some strange people between the ages of about 15 and 40 who don’t know the words to The Fresh Prince of Bel Air’s theme tune verbatim. Probably some miserable cretin who hasn’t ever smiled, or experienced the sheer joy of the Carlton dance. Someone for whom the pleasure of a Simpsons/Fresh Prince double bill on BBC 2 at 6pm on a Friday night wasn’t as important as watching Chris Evans being a laddish twat on TFI Friday and introducing shit indie bands that no-one remembers.

For the rest of us, truly cool people, this is arguably the defining cultural movement of our youth. Ish.

In any case, despite never being a critical darling or a ratings behemoth, The Fresh Prince of Bel Air has endured in a way that most TV shows starring people who became more famous later on haven’t. Why is that? What has The Fresh Prince of Bel Air got that Johnny Depp’s 21 Jump Street and John Travolta’s Welcome Back, Kotter don’t?

Maybe it actually is the theme song. And the Carlton dance. And Uncle Phil. And Hilary. And Jazz getting thrown out of the mansion.

  1. Summertime [DJ Jazzy Jeff & The Fresh Prince, 1991]

Of all the hits Smith racked up, both solo and with DJ Jazzy Jeff, you could argue that this is the one that it is absolutely fine to like without it being a guilty pleasure in the eyes of the supposed critical elite.

Summertime saw DJ Jazzy Jeff & The Fresh Prince temporarily mature. It has been rumoured for years that Rakim was the ghostwriter of Smith’s lyrics, but Jazzy Jeff maintains this isn’t true. He told the Village Voice in 2011; “Will was always very hyper and I told him, ‘Bring it back. Vibe with it.’ And when he did that, everyone was like, ‘Wow. He sounds like Rakim.’ From the first day we played the record for people, they thought it was Rakim. When we first released it, everyone was like, ‘Did you hear that new song that Rakim did?‘”

It is based on a Kool & The Gang track called Summertime Madness, back when Kool & The Gang were a truly funky band, before adopting the more radio-friendly pop/disco sound most people associate with them. It genuinely jams, to an almost jarring degree.

It is probably the only track that has truly endured, and you are still likely to hear it every summer. Rightly so. It smells exactly like freshly cut grass.