Over the weekend, he picked up five Grammys for his massive diss track “Not Like Us,” including Record of the Year and Song of the Year.

The star-studded audience, including Beyoncé and Taylor Swift, were particularly enthusiastic about Lamar’s victories.

As he walked onstage to receive the Record of the Year Grammy in a seemingly intentional all-denim outfit known as a “Canadian tuxedo,” you could hear the crowd rap along to the song as it played throughout the arena.

The entire moment was a nice boost for the months-old diss track and a reminder of Lamar’s import leading up to the biggest gig of his career this weekend: headlining the Super Bowl LIX halftime show.

This won’t be Lamar’s first time on the NFL’s big broadcast.

In 2022, he appeared in the halftime show’s first-ever hip-hop lineup, alongside Dr.Dre, 50 Cent, Snoop Dogg, Eminem, and Mary J.Blige, where he performed his 2015 political anthem “Alright.” Lamar’s segment was a standout in a rather chaotic medley, due to his energetic stage presence and poignant visuals.

Even with the halftime show’s mediocre track record with rap, it felt inevitable that he would grace the telecast again at some point.

Lamar arguably could’ve taken on the show by himself years ago.

However, “Not Like Us” provided the perfect moment of organic enthusiasm and renewed respect for the critically acclaimed artist.

Still, his coming performance brings up a number of questions, from what happened to his previous concerns about the NFL to if he’ll even be able to play his hit song, which is currently the subject of a defamation lawsuit.

Here are five questions you might have about this year’s highly anticipated Super Bowl headliner and what may or may not go down on Sunday, answered to the best of our ability.

Lamar’s Super Bowl halftime show will most likely be historic for quite a few reasons, but a big one is that he’s the first solo rap act to headline the show in the broadcast’s almost 60-year history.

The music segment has certainly evolved since the early days of hosting college marching bands and the unsettling, feel-good dance group Up With People, now welcoming contemporary pop acts from Lady Gaga to The Weeknd.

However, the NFL has been more hesitant to fully embrace rap, despite it being one of the most popular genres of music in the world.

Even with its diverse talent, the show has historically catered to or at least made decisions based on its largely white viewership with inoffensive, apolitical artists.

That said, when obscene moments — like Justin Timberlake exposing Janet Jackson’s nipple in 2004 — and political messaging — like Beyoncé honoring the Black Panther Party in 2016 — have occurred on the halftime show, NFL viewers and the league itself have responded in histrionic ways.

In addition to the wave of backlash from conservative media, the Federal Communications Commission received numerous complaints about Beyoncé’s “Formation” performance.

Meanwhile, the NFL sued musician M.I.A. for $16 million in restitution after she extended her middle finger during Madonna’s halftime show in 2012.

While rappers like Nelly, Big Boi, and Nicki Minaj have appeared in a guest capacity, it wasn’t until 2022 that hip-hop dominated the stage.

It’s a decision that seemingly wouldn’t have happened if not for a recent partnership between the NFL and Jay-Z’s Roc Nation Entertainment.

Since 2020, Roc Nation has co-produced the halftime show with a notably diverse mix of guests, including Jennifer Lopez and Shakira, Rihanna, and, most recently, Usher.

That said, Lamar’s headlining might just normalize more hip-hop acts getting booked for the show.

Why is Lamar getting a halftime show now?.

2024 was an unexpected moment of hypervisibility for Lamar, thanks to a highly publicized beef with Drake.

While Lamar had been sneak-dissing Drake for nearly a decade, taking shots at his “fake” rap persona to his alleged habit of using ghostwriters, Lamar’s guest verse of the Future and Metro Boomin’ song “Like That” made his self-proclaimed hatred for the Canadian rapper known in a way it hadn’t been before.

The relatively tame “F— the Big 3” bar on the track kicked off a weeks-long back-and-forth between Drake, Lamar and an entire Avengers-like ensemble of Drake’s industry adversaries.