Timothy William Westwood is an English DJ who defines the sound of hip-hop for BBC Radio 1 for nearly two decades before going back to Capital Radio. He also hosted Pimp My Ride UK for MTV UK and rose to prominence in the Internet age for videos of the hottest freestyles on that side of the pond. Here are the 20 best prior to 2020.
20. Kendrick Lamar
Anytime K-Dot blesses the mic, you know it’s going to be fire. This is a short session compared to some of the GOATs, but it’s still a classic Kendrick verse.
19. Childish Gambino
Sure, he’s using his cell phone for some of it, but we all know 99% of these “freestyles” are written. It’s cool, so long as it’s a hot rhyme, which Gambino brings every time.
18. The Fresh Prince
Will Smith is a good-guy rapper who never gets the respect he deserves, but this clip reminds us how legendary both he and Westwood are.
Hova drops a fire freestyle in 1999, prior to the internet, but thankfully Westwood has a deep archive.
Wale Has a pair of freestyles, with his longer one being an instant classic over a variety of beats.
It’s easy to forget Tyga is talented AF, thanks to his falling out with Cash Money and association with to the Kardashians through Kylie Jenner. This freestyle is better than most rapper’s album verses, recorded while still on Cash Money.
14. Lil Dicky
The Jewish rapper spits some hot punchlines in this classic Westwood freestyle.
13. Rae Sremmurd
Slim Jxmmi and Swae Lee have hip-hop in their blood, which they prove by spitting 20 minutes of hot bars.
12. Machine Gun Kelly
MGK kicks a hot rhyme over Jay-Z’s Izzo beat in 2012 while he was still riding a high from being signed by Bad Boy. He comes back four years later still spitting flame.
11. J Cole
J Cole brings fire spitting that conscious rap with a street edge. You can tell he’s having fun, especially when Wu Tang’s Cream comes on.
10. Juice WRLD
Juice WRLD puts in an hour of work freestyling twice. It’s like getting two original mixtapes just for Tim Westwood.
9. A$AP Rocky
A$AP Rocky has a pair of hot freestyles from Tim Westwood, and each time is worth a listen.
8. Lupe Fiasco
Lupe Fiasco always gives you an education and wins on content alone. He’s like the Bernie Sanders of rap, constantly spitting truth. He’s one of few that actually sounds like he’s freestyling off the top of his head too.
7. Wu Tang
Method Man, U God, and Masta Killa go on for 10 minutes of hot Wu lyrics that bring you right back to the 1990s.
Hopsin has a set of great freestyles (although the one above is his best) that prove his lyrical ability beyond the doubt of any haters.
5. Kid Cudi
Kid Cudi’s flow in this 5-minute freestyle is on point. It’s a fast beat, and he has no issues keeping up with it.
4. Mac Miller
The late, great Mac Miller has a smooth fly that works on a variety of beats. He has a lot more energy in his second round. It’s a reminder of the genius that he was before he killed himself.
3. Big Sean
Big Sean is one of the most underrated rappers in the game. His lyrical game and flow in this freestyle is one of the best. I love hearing him emulate Meek Mill on I’m a Boss. It’s a shame it’s censored.
Skepta holds it down for the U.K. every time he blesses the mic. It’s a reminder that hip-hop is a worldwide phenomenon. If you’re not already familiar with this Nigerian-born grime king, you’ll fall in love with one of these verses.
Slim Shady is the undisputed goat of Tim Westwood freestyles, with a handful of epic rhyme sessions that’ll immediately remind you how Marshall rose to the top of the rap game in the first place.