It's been seventeen years since Justin Timberlake, then with his band *NSYNC, joined Britney Spears and Aerosmith at the Super Bowl Halftime Show in 2001. And it's been fourteen years since the word "Nipplegate" was etched into our collective pop culture lexicon after the Justified singer ripped off part of his co-performer Janet Jackson's bodice in 2004, briefly exposing her breast on national television. Both performances went down in American entertainment history, of course—albeit for two very different reasons.

This Sunday (February 4), Timberlake will return to the Halftime Show stage for a headlining set at Super Bowl LII in Minneapolis. The performance, set just two days after the release of the artist's fifth studio album, Man of the Woods, will once more position Timberlake—two decades after making his boy band debut—alongside iconic solo Halftime Show headliners like Madonna and Michael Jackson.

He'll have only thirteen minutes to live up to his participation in Super Bowl XXXV's dazzling multi-performer lineup, as well as redeem himself for his role in Super Bowl XXXVIII's media frenzy-causing snafu—a performance that was actually pretty great before all hell broke loose. But what can the pop star do to take his headlining set to the next level in 2018?

While the 10-time Grammy winning chart-topper is an undoubtedly exciting solo headline draw in his own right, over the years Timberlake has teamed up with countless genre-spanning music superstars, many of whom could certainly elevate his Halftime Show set to pop history-making proportions. The singer would benefit from enlisting the onstage help of some of these music heavy-hitters, from Drake, T.I., Pharrell and Rihanna (who, by the way, is long overdue for her own Super Bowl set) to country musician Chris Stapleton, who features on Timberlake's most recent single, "Say Something."

He'd also be sorely remiss to not invite longtime collaborator and producer Timbaland — largely responsible for the pop star's post-NSYNC solo chart success — onto the stage with him. Another excellent onstage team-up? Considering his and Timberlake's long-withstanding artistic relationship ("Suit & Tie," "Holy Grail," etc.), Jay-Z is a possibility—though it's rumored that, as an act of solidarity with NFL star and social activist Colin Kaepernick, the rapper already turned down an opportunity to perform at Super Bowl LII.

Of course, the big question is whether or not Jackson might, just maybe, make an appearance. It's highly unlikely at this point — especially considering Timberlake's disappointing refusal to acknowledge the part he played in Jackson's post-Nipplegate entertainment industry witch hunt — but it would make for a much-deserved moment of justice for Jackson, as well as pave a healthy path of redemption for Timberlake, who, some say, has been successfully co-opting black music for nearly two decades.

Super Bowl XXXVIII: Panthers v Patriots
Donald Miralle, Getty Images

To be fair, Timberlake did address the controversy earlier this year, telling Beats 1's Zane Lowe that he and Jackson eventually spoke about the incident and resolved the issue privately.

One less mystery is whether or not Timberlake will reunite with *NSYNC and bring former bandmates Joey Fatone, Lance Bass, JC Chasez and Chris Kirkpatrick on stage at some point during his set. Fatone recently told TMZ it isn't happening. The last time the group performed together was five years ago during the MTV VMAs in 2013.

However, an onstage reunion with his former bandmates would be smartly timed: the boy band released their debut self-titled album in the United States nearly twenty years ago, in March 1998. Much like how Beyonce reunited with her Destiny's Child sisters at the 2013 Halftime Show nearly a decade after the group released their final album together, a surprise NSYNC medley would make for a much talked-about moment—as well as serve as a thrilling climax to the Halftime Show, which has been hit-or-miss in recent years.

Musical Performers at Super Bowl XXXV
Jonathan Daniel, Getty Images

As for Timberlake's performance, barring any aforementioned potential collaborations, the artist would benefit by focusing on fan favorites and bona fide smash hits versus newer cuts or covers. Familiar songs like "SexyBack," "Rock Your Body," "Suit & Tie," "Cry Me a River," "My Love," "LoveStoned" and "Can't Stop the Feeling" would make for an energized set suited for longtime fans and general Super Bowl viewers alike.

And if an *NSYNC reunion does come to fruition during the star's set, a colorful medley of classic '90s and '00s hits— think "Tearin' Me Apart," "Pop," "It's Gonna Be Me" and "Bye Bye Bye"—would do the trick, tapping into the pulsating vein of nostalgia's 20-year cycle.

Song choice aside, the overall memorability of Timberlake's set will depend on set production. Unlike previous performers Lady Gaga and Katy Perry, whose glamorous, sparkly and playful sartorial elements lent to the spectacle of their sets, Timberlake isn't known for his over-the-top style. Instead, the singer should invest his creative planning in building out an immersive set rife with effects — think pyrotechnics and moving stage parts — that can draw viewers into the thrill.

No matter what Timberlake does during his Halftime Show set, the pop star has undoubtedly earned his Super Bowl laurels. On Sunday night, we'll see how he chooses to wear them.

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