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Every time Tyler, the Creator decides to freestyle, it turns into a spectacle. He has repeatedly said that he hates the radio freestyle format, so when he agrees to do them, he usually ends up making a mockery of the whole situation. Back in his early days doing press circuits with Odd Future, Tyler began adopting the exaggerated characteristics of stereotypical New York rappers and delivering wild parody freestyles. These moments are always a little awkward for the radio hosts, but endlessly enjoyable for those of us watching at home. From his early days recording 2008 freestyles in his home as a teenager to his viral 2019 Funk Flex appearance on Hot 97, these are Tyler, the Creator's best freestyles.
Tim Westwood Crib Session Freestyle (2013)
"Oh, you wanna see what a wild boar sounds like?" Tyler asks Tim Westwood, as he sits on the floor at the beginning of his Westwood Crib Session. Throughout the six and a half minute video, Tyler talks about bacon, says the word "baby" over and over, raps in an unrecognizable language, digs for old Ashanti records, and barely ends up getting around to actually freestyling. This might be the one time that his antics go so far they detract from what could have been a more entertaining moment with a little more focus (which is why it ended up so low on this list) but the Tommy Pickles reference makes the whole thing worth a watch. —Eric Skelton
Teenage Selfie Freestyle (2008)
Back in 2008, a young Tyler uploaded a freestyle to his YouTube channel while he was bored in Sacramento. He seems like he’s being relatively serious here, but you probably couldn’t tell because his raps are as ridiculous and explicit as every other freestyle on this list. He’s obsessed with incest, guns, and body parts. This video is more than a decade old, but it’s clear some things never change. If you're interested in hearing more self-recorded teenage freestyles, check out his outdoor Sacramento freestyle and his secret garden freestyle. —Jessica McKinney
Bus Freestyle (2011)
Some of this freestyle isn’t even in English (or any language for that matter), but it’s entertaining nonetheless. Tyler and Odd Future’s Jasper Dolphin exchange bar for bar on a tour bus and things get weirder than weird around the one minute mark, when the two have a contest of who can say the most gibberish. The best part about this is one is Tyler screaming “oh” at least 10 times after his first bar. What this freestyle makes up for in substance (and camera quality), it makes up for by giving us an inside look at what it was like to hang with these guys in the early Odd Future days. —Jessica McKinney
Power 106 Open Bar Freestyle (2014)
Tyler, the Creator put his improvisational skills to the test during Power 106’s Open Bar freestyle series when the hosts called on him to spit about four random topics over OG Maco’s “U Guessed It” instrumental. And the topics in question were just as absurd as you could have hoped for: grandmas, pregnant girls, bacon, and groupies. In true Tyler fashion, he approached each word with enthusiasm and bizarre raps: “Bitch, open up your fucking book and let me lick that page / But wait a minute, that shit clean? Let me get spray out of the bathroom.” The segment goes by quickly, perhaps because Tyler had to use the bathroom the whole time, but he gets points for creativity and managing to work humor into his most serious radio freestyle. —Jessica McKinney
SBTV Freestyle with Hodgy Beats (2011)
A young Tyler delivers some of his most lyrically diverse bars in this 2011 a cappella “freestyle” with Hodgy Beats. This one sticks out from the rest because Tyler is rapping his ass off and taking things seriously, but it slid farther down the list because it lacked that air of fun and off-the-top spontaneity that his freestyles are known for. Here we see Tyler actually focusing on his rhymes, rather than sticking to his trademark style of sporadically spitting whatever comes to mind first. This is Tyler, the Creator we're talking about, though, so he still manages to fit in some hilarious one-liners: “My mom caught me jacking off to Hannah Montana with a banana peel.” What?! —Jordan Rose
Terry Richardson Odd Future Freestyle (2012)
The Odd Future crew, led by Tyler and Earl Sweatshirt, are at their absolute early peak in this freestyle at Terry Richardson's studio. They’re having fun, laughing, and gassing each other up. Tyler, for his part, delivers tough guy rhymes one after the other, cracking up the assembled crew with intentionally retro-sounding punchlines like "The AK-47 leave a n***a holy/Red sauce on his shirt, bowl of ravioli” that, in a different universe, could easily have come from a lost mid-aughts Jadakiss/Styles P duet. In general, Terry Richardson is a person I’d rather not talk about, except to say that you should read up on the long history of sexual assault and abuse allegations against him. But if you must watch one thing on his TerryRichardsonTV YouTube channel, it should be this. —Shawn Setaro
Sway in the Morning Freestyle (2013)
In the fall of 2013, Tyler stopped by Sway In The Morning to promote Wolf. Joined by Jasper and Taco from Odd Future, Tyler finally gives in to pressure from Sway and bodies a quick freestyle. Starting the verse very cool and monotone, he adopts the persona of his Young Nigga alter ego and raps lines like, "Nigga know his bitch a bitch/And I'm a dog I give that bitch a bone." Then, he sounds like an over-eager puppy as he literally barks: "Arf, Arf, bark, bark can't see a nigga in the dark, dark." Legend. —Zoe Johnson
Hot 97 Freestyle with Vince Staples (2015)
Even though Vince Staples wasn’t an official member of Odd Future, his close relationships with Earl Sweatshirt, Tyler, and Syd often brought him in the presence of the entire collective. One of the most memorable examples of this was his joint appearance with Tyler on Hot 97 back in 2015. Vince kicks his freestyle off with bar quality so high that he could’ve later released it as a standalone track, but Tyler still found a way to steal the show. "No matter what happens, the result is good," Rosenberg said before Tyler started. He was right. Tyler ends up jokingly ripping the Lil Kim beat while addressing his relationship with Vince, GOLF, and claiming that Peter Rosenberg is the fat Eminem. Bars. Did you peep how hard Tyler was bouncing when he was rapping? I guarantee you’ll do the same when you listen. —Kemet High
H.A.M. Sandwich Freestyle with Peter Rosenberg (2012)
Whenever Tyler links up with fellow Odd Future members Earl Sweatshirt and Domo Genesis in a radio station, madness is about to break out. Give them JAY-Z and Kanye West’s "H.A.M." instrumental, and you are left with a masterfully hilarious performance like this one. The three do their best “Throne” impersonation and literally freestyle about making a ham sandwich for Peter Rosenberg on Hot 97. First, you have Earl laying out the appropriate ingredients for a ham sandwich on the impromptu hook, before Tyler follows up by snapping on the beat (Kanye ad-libs included). Domo Genesis also chimes in by rapping about literally nothing related to what the previous two were talking about. Honestly, this freestyle makes you curious as to what an Earl, Tyler and Domo project would sound like if they rapped exclusively about lunch dishes. Lunch meat aside, this is a perfect example that the more fun Tyler has, the better his freestyles are. —Jordan Rose
Funk Flex Freestyle (2019)
Tyler, the Creator showed up to meet Funk Flex for the first time in July 2019 and he had no idea what to expect. What followed was one of the most compelling rap interviews of the past decade, as the two poked and prodded each other until they bonded over shared nerdy interests (Flex collects baseball cards??) and became unexpected "besties." Then, the freestyle happened. A continuation of the 80-minute conversation that preceded it, Tyler trolled Flex and took him out of his comfort zone (on his own show!) with off-the-top lines like, "Me and Flex looking in the index/For buff net n****s just for some hot butt sex." What pushes this to the No. 1 position on this list, though, is the way Tyler masterfully weaves his trolling attempts into legitimately impressive bars. For every one-liner he uses to bait Flex ("Like R Kelly, wet dreams, I always keep 16s") there's an equally sharp rhyme on the more serious side of things ("Lookin' for them tweets, bitch, find it/The cancel couch is fake, and I recline it"). After fucking around at radio stations for nearly a decade, Tyler pulled together all his greatest strengths and delivered a wildly entertaining freestyle that easily ranks as one of 2019's best pop culture moments. —Eric Skelton