Must-See TV! 25 Wildest Award Show Moments - Page 5

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.

RELATED: 10 Most Memorable Black Hosts At Award Shows

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!

Keep scrolling for our picks of the 25 wildest awards show moments ever. Let us know if there’s any you can recall that we might’ve missed:

1. Eddie Murphy and Joan Rivers Get Themselves Banned From Hosting Award Shows (1983 Emmys)

2. Vanilla Ice Gets Booed And Embarrassed By The Industry (1991 Soul Train Awards)

3. Michael Jackson Shares The Most Awkward Kiss With Lisa Marie Presley (1994 MTV Video Music Awards)

4. Onyx Shoots A Real Gun Mid-Performance (1994 Source Awards)

5. Suge Knight Challenges Bad Boy Records Live On Stage (1995 Source Awards)

6. Aretha Franklin’s Unforgettable 11th Hour Opera Fill-In For Luciano Pavarotti (1998 GRAMMYs)

7. Diana Ross Gets Handsy With Lil’ Kim’s Pastie (1999 MTV Video Music Awards)

8. Jennifer Lopez Invents Google Images With A Dress (2000 GRAMMYs)

9. Nelly Risking It All For A (Single Lady?) Beyoncé (2000 Source Awards)

10. Whitney Houston Thanks Everybody, Blesses The Newcomers and Proves Why We Love Her (2001 BET Awards)

11. Michael Jackson Makes Up His Own Award (2002 MTV Video Music Awards)

12. Anna Nicole Smith Is Wasted From Head-To-Toe While Introducing ‘The Old Kanye’ (2004 American Music Awards)

13. Destiny’s Child Make Nelly, Terrence Howard & Magic Johnson The Luckiest Men Alive (2005 BET Awards)

14. Three 6 Mafia Break The Dress Code And Status Quo (2006 Oscars)

15. Jamie Foxx and Fantasia Forget The World Is Watching (2006 BET Awards)

16. Kanye West Interrupts Taylor Swift At The Podium (2009 MTV Video Music Awards)

17. “Brüno” Violates Eminem…Or So We Thought! (2009 MTV Movie Awards)

18. Lee Daniels Helps A Drunken Mariah Carey Accept An Award (2010 Palm Springs International Film Festival Awards)

19. Beyoncé Reveals Her Blue Ivy Baby Bump (2011 MTV Video Music Awards)

20. “Miley, What’s Good?” (2015 MTV Video Music Awards)

21. Steve Harvey Gets The Winner Wrong (2015 Miss Universe Pageant)

22. The Ever-So-Viral Chrissy Teigen Crying Face (2015 Golden Globe Awards)

23. The Big “Best Picture” Mix-Up (2017 Oscars)

24. Will Smith Slaps Chris Rock (2022 Oscars)

25. When Ariana DeBose “Did The Thing” (2023 BAFTAs)