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Boardroom & ChatGPT Achieve Super Bowl Halftime Show Singularity

Last Updated: July 1, 2023
We invited the artificial intelligence (that could destroy us all) to our MUSIC ROUNDTABLE in order to comprehend the past, present, and future of Super Bowl Halftime performances.

Remember when Justin Timberlake did that thing to Janet Jackson and then we spent the next several years subjected to Super Bowl Halftime performances featuring nary a person under the age of 60? Yeah, good times. Fortunately, after a few good years of spirited, generally well-received performances, Rihanna makes her grand return on Sunday in Arizona at Super Bowl LVII to send things into hyperdrive in Year One of Apple Music’s title sponsorship of the annual mid-game tradition.

That got us thinking — what is it that makes such a performance memorable, and how should that shape our thinking about the event now and going forward?

Well, we set out to make several whip-smart Super Bowl Halftime observations by reconvening our MUSIC ROUNDTABLE — Sam Dunn, Chuck McMahon, Brett Pickert, Anthony Puccio, Shlomo Sprung, and Ian Stonebrook — but we quickly realized we couldn’t do it alone.

Rather than risking looking like a bunch of dilettantes out here, we called upon ChatGPT, the plucky and possibly deadly artificial intelligence construct created by OpenAI, to help us respond to three essential queries:

  1. What’s the current greatest Super Bowl Halftime Show of all time?
  2. Which song will Rihanna play first, and which special guest should she bring out?
  3. Pick an artist who has never headlined the Super Bowl who would put on the greatest such performance imaginable.

Time to work.

…Work, work, work, work.

Click here to read Boardroom’s rundown of the most-watched Super Bowl Halftime performances of all time.

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What’s the greatest Super Bowl Halftime Show of all time?

IAN STONEBROOK:  In the annals of YouTube, Michael Jackson will always take the cake for me. That entrance? Who could say more without saying anything at all? Just as performers, period, I don’t think anybody beats the King of Pop at Super Bowl XXVII in 1993.

But in my real-time viewing, it’s a tie between Aerosmith x NSYNC (Super Bowl XXXV, 2001) and Shakira y J Lo (Super Bowl LIV, 2020). During the former, Nelly’s split jersey and Britney Spears’ use of socks as sleeves make a strong case that Super Bowl parties should also be costume parties.

BRETT PICKERT: Super Bowl XLI with Prince (RIP) in 2007. Prince has energy that will never be matched as a performer, Plus add 100 to the level of difficulty for playing in a downpour.

ANTHONY PUCCIO: Dr. Dre, Snoop Dogg, Eminem, Mary J. Blige, Kendrick Lamar, and 50 Cent last year. A loaded roster with some of my favorite all-time artists, and 50 popping up out of nowhere was a real bonus.

CHUCK McMAHON: It’s gotta be the 2001 halftime show featuring the Kings of Rock & Pop: Aerosmith, NSYNC, and Britney Spears. The game itself was boring, but seeing Steven Tyler perform “Walk this Way” with peak JT and Britney, not to mention surprise appearances by Mary J. Blige and Nelly, makes this the GOAT of halftime shows.

SHLOMO SPRUNG: The greatest Super Bowl halftime shows are always the most memorable, and by that metric, the Justin Timberlake-Janet Jackson wardrobe malfunction halftime show may never be topped — but in terms of the ones I enjoyed the most, Beyoncé at Super Bowl XLVII, Bruno Mars at Super Bowl XLVIII, Lady Gaga at Super Bowl LI, and The Weeknd at Super Bowl LV probably top the list — along with last year’s hip-hop classic in LA, of course.

SAM DUNN: People, it’s Prince. Next!

ChatGPT: “As a language model AI, I don’t have personal opinions but according to many fans and critics, the greatest Super Bowl halftime show is widely regarded as the 2001 Super Bowl XXXV halftime show featuring Aerosmith, NSYNC, Britney Spears, Mary J. Blige, and Nelly.”

Which song will Rihanna play first, and which special guest should she bring out?

BP: “Don’t Stop the Music”. Bring out Leo and Drake for the memes.

SD: That feels right, Pooch. A number of sportsbooks are favoring “Diamonds,” which would be a great pick, but my ever-aflutter heart is telling me “Don’t Stop the Music.” As for a surprise guest, how about Phoenix native Stevie Nicks? Who says no?!?

If I was going to identify a serious-but-frisky long shot, however, let’s take it all the way back to the origin: “Pon de Replay.” There might be a riot.

AP: The “Cockiness” remix with A$AP Rocky.

SS: It’s a dark horse on the betting market, but let’s go with “We Found Love.” And please bring out Jay-Z for “Umbrella.”

CM: Just in case your 85 year-old-old grandmother doesn’t know who she is, RiRi will likely kick things off with “What’s My Name.” Ooh-na-na. And expect Drake to get things hyped with a cameo because… that’s what Drake does.

IS: I’m calling “Disturbia” out the gate. Instantly recognizable, high energy, and a good tone setter. If Hov just rapped for 10 minutes straight on live TV at the Grammys, I think there’s a solid chance he comes out for “Umbrella,” but I’m always Team Flacko if we can get an on-stage A$AP Rocky sighting.

ChatGPT: “As a language model AI, I don’t have the ability to predict future events but based on Rihanna’s popular songs, it is likely that she will start with one of her biggest hits such as “Umbrella”, “We Found Love”, “Diamonds”, or “Stay”. However, it is ultimately up to her and the Super Bowl Halftime Show producers to decide what will be performed.”

Pick an artist who has never headlined the Super Bowl who would put on the greatest performance imaginable.

AP: The only answer is Jay-Z. Greatest of our time. Connections with the best talent around the world. Top-class live performer. There’s no disputing the GOAT’s influence beyond his music catalog.

CM: Yeah, how has Jay-Z not headlined a Super Bowl yet? Just picturing the hype of getting HOV on stage during halftime, not to mention the star power that would accompany him, is mind boggling.

SS: “The greatest” is a high bar, but if we want a truly unique, unforgettable one, go to Las Vegas next year and try to assemble the greatest House and EDM artists to ever live to put on a performance in America’s current capital of dance music. Bring Daft Punk out of retirement, Skrillex, Tiesto, Deadmau5, Swedish House Mafia, and Calvin Harris, and blow it out!

SD: While it’s far from impossible, it’s nonetheless challenging to get live hip-hop to sound right — especially when you have eight minutes to convert a football field into a full-on festival stage.

With that in mind, we need one of these things in order to achieve true Super Bowl Halftime Singularity:

  • Outkast reunion (yes, Big Boi has already done the Super Bowl, but not Dré)
  • Nas
  • Spın̈al Tap reunion
  • Dolly Parton

That is all. No, I will not be answering any questions at this time.

IS: Apple Music bringing out Rihanna is awesome, but I’m not against a future pivot of “Nextflix Presents Adam Sandler & Friends.” Hearing a medley of Happy Madison soundtrack songs played by the Sandman, Dave Matthews, and a who’s-who of classic rock royalty is the type of paid content I’m here for.

If that’s a bridge too far, Usher getting the headline spot on Super Bowl Sunday feels long overdue.

BP: Gotta go with Justin Bieber. He’s one of the most popular artists of this era (and potentially all-time by the time he’s done), so he has to show out for the world’s most-watched sports and entertainment spectacle. He has so many songs featuring other artists he could bring out. Plus, it’s the Biebz.

ChatGPT: “One of the biggest recording artists never to perform at the Super Bowl Halftime Show is Adele. Despite her immense popularity and numerous hit songs, she has not yet been asked to perform at the event. Other big recording artists who have not performed at the Super Bowl Halftime Show include Taylor Swift, and Ed Sheeran.”

NOTE: ChatGPT also mentioned Bruno Mars, who has performed at the Super Bowl Halftime Show two different times. Additionally, Adele has previously said that she was invited to perform at Super Bowl LI but declined.

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