The Worst Freestyles of All Time – A Hilarious Trip Down Memory Lane

Freestyling has long been an essential part of hip-hop culture, showcasing an artist’s ability to think on their feet, deliver clever wordplay, and prove their lyrical skills. However, not every rapper can master the art of the freestyle, and over time, we’ve been gifted with some unintentionally hilarious—and downright awful—attempts. In this video, we take a deep dive into some of the most cringeworthy freestyles ever, featuring a lineup of artists ranging from unexpected flops to rap legends caught on an off day.

The countdown kicks off with SmokePurpp, whose freestyle is the embodiment of mumble rap at its most puzzling. From forgetting lyrics to delivering bars that barely make sense, it’s a perfect start to a collection of freestyles that should’ve stayed in the drafts.

Iggy Azalea’s entry (4:10) is another memorable trainwreck, reminding us of her infamous Sway in the Morning performance that left the internet in tears—of laughter. The lack of rhythm and coherence in her delivery makes it one of the most talked-about freestyles in modern rap history.

Even big names like Drake (6:35) and The Game (8:14) aren’t safe from scrutiny. While they’ve both built impressive rap careers, these particular moments prove that even seasoned artists can have an off day. Drake’s freestyle struggles highlight his strength as a songwriter rather than an off-the-dome lyricist, while The Game’s lack of energy and uninspired bars make for an uncharacteristically weak performance.

One of the most surprising entries is Machine Gun Kelly (MGK) (12:07), who’s typically known for his rapid-fire delivery. However, this particular freestyle doesn’t live up to his usual standards, proving that not every session in the booth results in a hit.

Perhaps one of the biggest shockers is Kanye West (21:28). Despite being a hip-hop visionary, Ye’s freestyle entry here is a mess of incoherent rambling, proving that his genius shines brightest in the studio rather than in impromptu rap sessions.

From Joe Budden (17:01) to Tsu Surf (20:07), the list continues with freestyles that are either painfully awkward, overly theatrical, or just plain bad. Coi Leray (24:10) also makes an appearance, highlighting the newer generation’s sometimes-questionable approach to freestyling.

However, one of the most bizarre and oddly captivating moments comes from Haiti Babii (27:33), whose freestyle is less about bars and more about experimental sound effects. Whether it’s avant-garde artistry or just a complete disaster depends on who you ask.

Overall, this video is a must-watch for hip-hop fans who love a good laugh at some of the most infamous freestyle fails. While these artists may have solidified their careers in other ways, these particular moments live on as reminders that not every freestyle session is a success.

A hilarious and entertaining breakdown of some of the worst freestyles in hip-hop history. A must-watch for rap fans who enjoy a little nostalgia and comedy!