Who your lineups? Don’t try and think about the most popular rapper/singer to perform but the type of act that could probably control a crowd very well and has enough interesting songs/hits to keep a crowd that big rocking. Not gonna lie,I don’t necessarily have a lineup for two day,I definitely know who my headliners tho,here goes.

Headliners for Day 1-Outkast/Kanye West

Headliners for Day 2-Frank Ocean/Kendrick Lamar

Random list of guys/girls who I think would be a good fit to perform-Chief Keef,A$AP Rocky,Lil Wayne,Lana Del Rey,Soulja Boy(let him perform his old hits as a lowkey joke lol)Radiohead,Wiz Khalifa,Lil Uzi Vert,Playboi Carti,Kid Cudi,Odd Future reunion,Erykah Badu

If your interested,show me your list cause those are the only guys I can think of that could handle a show of this caliber imo.

I’d have Chingy perform for the entire event.

nah

That would take an impressive amount of false advertising to get that amount of people to actually show up my friend lol

Damn,nobody can come up with a lineup,jeez. Maybe my list is too good

Bob Dylan, Drake, Adele would do old town road numbers on steroids in attendance and viewership figures.

Ahead of his time with the transgender girl

LNX, drake, youngboy, carti, gambino, 69

Ed sheeran dua lipa adele

Bob Dylan a good choice but if you watch the Woodstock 99 doc on HBO,the promoters said that they were actually trying to kinda avoid the most commercial acts and get the peoplewho best fit the vision of Woodstock(liberation,ability to bring people together,non-commercialism etc.) Drake and Adele gotta sit this one out

Adele and Drake the only ones really outselling whole arena tours tho in 2022

And Woodstock 99 just had one big Jumbotron showing the stage,no theatrics or whatever,the performers were just on one huge stage performing in front of a ruckus huge crowd. No matter how big Drake or Travis is,it’ll be a huge task for any of them to control a crowd that big for let’s say almost an hour and a half of performance.

I think an OutKast reunion,a Kanye performance with him performing backlog stuff and Kenny/Frank giving full blown shows as headliners could easily sell whatever stadium you throw at it and could possibly be PPV worthy like the Woodstock’s from the 90s.(idk how possible any of this would be tho lol)

I didn’t even understand how insane this proposal really was. OutKast and Ye doing back to back full blown concerts in one night with Ye performing classics in his catalog i wanna speak this into existence. I’m sorry but it would really be criminal if something like that was a free live stream on YouTube.

I would pay PPV or make a real attempt to be their live for an OutKast/Kanye double headliner

Lmfao nah

Squidnice

playboi carti

Give me Frank Ocean, Kanye performing his greatest hits, a Daft Punk reunion show, and Radiohead headlining.

Limp Bizkit. Couldn’t be any worse than the first time?

1st performance at Woodstock was legendary(minus the crowd controversy),you don’t even have to like Limp Bitzkit to appreciate this performance

I wouldn’t want to see a reunion tho

A Daft Punk reunion vs an OutKast reunion is a tough choice,both are more than headline worthy tho.

I hope you know I pack a chainsaw!!!!

Drake would definitely be the best headliner for day 2 in your hypothetical scenario.

We talking Woodstock coming back and mans said an odd future reunion

Hey,I’m just throwing names out there,the headliners are the real meat