#1: Tyler Freestyles on Sway in the Morning (2013)
The hottest freestyle on the list is also one of the shortest. Tyler made an appearance on Sway in the Morning back in 2013 about a month before releasing his second album, Wolf. When asked about the new album, Tyler responded by shitting all over it as only Tyler would: “I focused in and tried to craft the worst shit i could possibly make. The album sucks… I think I just naturally lost that spark that I had and it just sounds like complete shit.”
Sway goes on to ambush Tyler with a beat to freestyle over and Tyler goes absolutely ham. His bars actually get better and better the longer he goes – a trend that we see throughout the rest of his freestyles too.
#2: Tyler Freestyles Four Bars Four Topics (2016)
If you ever wanted to hear Tyler rap off the dome about grandmas or bacon, your dream has finally come true.
Tyler gets four topics to freestyle on, one after another, over the beat for Bitch U Guessed It by OG Maco. Each new verse is better than the one before it. The best part? Tyler going off about fucking groupies for over a minute at the end.
#3: Tyler Freestyles, Puts Vince Staples to Shame (2015)
Tyler, the Creator and Vince Staples take turns freestyling together on Real Late with Rosenberg. Vince Staples goes first and he isn’t horrible, but he’s clearly uncomfortable with going off the dome. Vince ends up spending more time thinking about the beat than he actually spends spitting. It’s hella anti-climactic and borderline cringe-worthy.
After Vince bombs out for the second time, Rosenberg throws it over to Tyler. Once Tyler gets his flow down about 20 seconds in, he grabs it and goes all out for nearly two minutes straight. Hopefully Vince learned a few things.
#4: Tyler’s Full A Capella Freestyle on Sway (2013)
This freestyle even got Sway a little afraid. Tyler’s a capella freestyle is a continuation of the first video on our list and will put goosebumps straight down your back.
Sway sums it up pretty well: “Damn. That’s the hardest shit I’ve ever heard”
#5 Tyler Freestyles off the Dome at Camp Flog Gnaw (2016)
Tyler performs “Rusty” with Earl Sweatshirt and Domo Genesis at his music festival in 2016. Cut to 1:48 to see Tyler forget one of his verses and start going off the dome while Earl headbangs and the crowd goes wild. He only goes for about 30 seconds but those 30 seconds are hard as hell.