Today and Saturday, Jay-Z and Justin Timberlake take the stage at Yankee Stadium for their Legends of Summer tour. While they’re both certainly living legends in their own right, it’s interesting to look back on how truly different both Hov and Timberlake’s summers have been over the years, and yet both paths lead to this weekend’s shows. Let’s take a look back at 20 years of summer fun for the two.
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Original Flavor featuring Jay-Z “Can I Get Open” 1993
The Mickey Mouse Club: Justin Timberlake and Ryan Gosling meet Xscape 1993
We all had to start somewhere. For some of us, it’s kicking quick-tongue 5% doctrine on the corners of Brooklyn. For others, it’s singing the classics at Disney MGM Studios. While Jigga had been putting out singles since 1986’s “HP Gets Busy,” his first major appearance (no, “Hawaiian Sophie” doesn’t count) was joining Original Flavor for the fun cult classic “Can I Get Open.” It’s hard to believe the “J-kickin-the-A-rippin-it-way-past-Y,” while dope, would go on to be one of rap’s biggest trendsetters. It’s a little easier to fathom the pint sized enthusiastic Timberlake growing up with our nation’s teens and later stealing all of our hearts on Saturday Night Live.
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Jay-Z – “Hard Knock Life” 1998
N*SYNC – “Tearin’ Up My Heart” on TRL 1998
The summer of ’98 saw both Timberlake and Jigga beginning their ascension into full-blown pop superstardom. As the primary dreamboat of N*SYNC, Timberlake lead his group into scoring their first monster North American hit in “Tearin’ Up My Heart.” This coincided with the rise of MTV’s Total Request Live, allowing the pendulum of pop music to swing into the hands of teenagers with access to phones and AOL Keyword: MTV. Also appearing on the TRL countdown was Jay-Z, whose Annie sampling “Hard Knock Life” had managed to crossover to a pop audience without even trying to crossover, making his album Vol 2…Hard Knock Life become the biggest selling of his career.
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Beyonce featuring Jay-Z – “Crazy in Love” live on BET Awards 2003
Justin Timberlake – “Cry Me a River” live at Billboard Music Awards 2003
The two dominated their respected realms of popular music for the next five years, simultaneously entering a projected maturity in 2003. While Timberlake had finally broken out from the N*SYNC boy-band restrictions into a full-fledged respected solo artist, thanks in part to the productions of The Neptunes and Timbaland, Jay put the wheels in motion to solidify his legacy. After joining fiancee Beyonce for her first solo single and solo performance at the BET Awards, making him a mainstay of any pop radio station that summer, he also began the promotional trail spreading the word that his forthcoming project The Black Album would be his final release before entering (his third) retirement. For listeners having grown-up with both artists, the summer of 2003 effectively made Jay-Z the icon of modern rap and Timberlake the icon of modern pop.
Jay-Z – “Wonderwall / 99 Problems” Live at Glastonbury 2008
Justin Timberlake in The Love Guru 2008
While the popular adage states when you’re at the top there’s nowhere to go but down, both Jay and Timberlake proved the other option was just going elsewhere for a bit, doing entirely incomparable projects. The summer of 2008 found Timberlake near the start of his seven year hiatus from music as he ventured into acting, at the time perhaps regrettably, in Mike Myers’ woeful bomb The Love Guru. Also facing criticism was Jay-Z who, two albums back from retirement, was publicly dissed by Oasis ball of sunshine Noel Gallagher, who found news of the rapper’s headlining the esteemed Glastonbury festival “wrong.” Jay responded by opening his set with a tongue-in-cheek cover of Gallagher’s “Wonderwall” before going into “99 Problems.”
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Jay-Z & Kanye West – “Niggas in Paris” 11 Times in Paris 2012
Justin Timberlake’s Tribute to Gene Kelly 2012
It’s kind of funny to think how both Timberlake and Hov’s new albums, two of music’s biggest stories of the year, didn’t even seem like a remote possibility a mere 12 months ago. While Jay was still riding high from the critical and commercial success of his collaborative album with Kanye West Watch the Throne, he performed the Steve Reich-ish feat of performing “Niggas in Paris” a whopping 11 times in a row live in Paris. Still, while Jay was creating an art-minded piece of repetition though music, Timberlake appeared to have everything but singing on his plate. Despite it later coming out that he had secretly been working on The 20/20 Experience all summer, Timberlake denied all reports of working on music, including his publicist specifically stating that there were no plans for a new album. The closest he came to anything music related was giving a touching tribute to Gene Kelly a few short weeks before secretly marrying Jessica Biel. Leave it to Justin and Jay to remind us how much hotter they make summer fun.