Must-See TV! 25 Wildest Award Show Moments

February 4, 2026 2

Awards Season is officially among us!

After a long year of chart-topping music releases, blockbuster weekends at the box office and everything in-between in the world of entertainment, now’s the time to see where the chips officially fall when it comes to giving out accolades of excellence.

Just recently, we saw the music world see their biggest night with the 2026 GRAMMY Awards, which saw first-time winners, some adding to their growing trophy case and, as expected, a handful of unforgettable moments. One in particular was the now-viral moment between “Best Progressive R&B Album” winner Durand Bernarr (BLOOM) and winner of “Best R&B Performance” and “Best R&B Song,” Kehlani (“Folded”) — each first-timers who’ve been going for the gold with zero success for over a decade.

It was heartwarming to say the least.

Something about that aforementioned GRAMMYs moment just tugged at our awards season emotional strings and reminded us of all those great moments from past ceremonies. From beloved musicians to the Hollywood elite, we’ve seen some of the most candid, some might even call crazy, and most what-the-helly moments to ever air on live television.

You’ll watch entertainers grow before your eyes on all levels as the years scroll down, and for sure get hit with a strong sense of nostalgia as you move along. A few highlights you’ll notice below include the beginnings of Kanye West’s downfall, hints that Nicki Minaj has probably always been this erratic, sweet memories of late legends like Michael Jackson and Whitney Houston alike, Beyoncé in all her fly eras and, well, some of the best-dressed Black people you’ve ever seen.

Enjoy the show!