With this year’s Academy Awards just days away, it’s time to relive some of my favorite Oscar moments from its 96 years! While there are so many moments to choose from, I picked the moments from the Oscar ceremonies over the years that live rent free in my head, these are the moments I best remember and often look back on and rewatch them. A lot of the moments remembered are from my younger years watching the Academy Awards, but that is how I know these are My Top Ten Oscar Moments, because I have remembered them all this time and never forget these Oscar Sunday memories!

Oscar Moments…

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10. Burt Bacharach “Best Original Song” Montage…

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At the 72nd Academy Awards, often called Oscars 2000, pianist, composer, songwriter, producer, and three time Oscar winner, Burt Bacharach performed a Best Original Song Montage featuring musical legends Garth Brooks, Faith Hill, Ray Charles, Queen Latifah, Issac Hayes, and Dionne Warwick on March 2, 2000. The montage received an enormous amount of attention before it even aired, Whitney Houston was originally scheduled to join her aunt, Warwick, in the montage but canceled after rehearsals that day did not go well, her people would say it was a throat problem, but years later we would understand it was her drug abuse that was beginning to effect her performances as her heath declined. Faith Hill was asked to replace her hours before the montage and sang the Oscar winning Best Song “Somewhere Over the Rainbow” instead.

Best Original Songs Featured:

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Garth Brooks – “Everybody’s Talking at Me” – Midnight Cowboy (1969)

Faith Hill – “Somewhere Over the Rainbow” – The Wizard of Oz (1939)

Ray Charles – “Secret Love” – Calamity Jane (1953)

Queen Latifah – “The Man That Got Away” – A Star is Born (1954)

Ray Charles – “I’ve Got You Under My Skin” – Born to Dance (1936)

Ray Charles – “All The Way” – The Joker is Wild (1957)

Garth Brooks – “Raindrops Keep Falling On My Head” – Butch Cassidy & the Sundance Kid (1969)

Issac Hayes – “Theme from Shaft” – Shaft (1971)

Faith Hill & Queen Latifah – “The Way We Were” – The Way We Were (1973)

Garth Brooks – “When You Wish Upon a Star” – Pinocchio (1940)

Burt Bacharach & Dionne Warwick – “Alfie” – Alfie (1966)

9. Kim Basinger wins Best Supporting Actress…

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Cuba Gooding, Jr. presenting Kim Basinger with the Best Supporting Actress Oscar for her performance in L.A. Confidential at the 70th Academy Awards in 1998 is a great moment, not only does Gooding Jr. make reference to his memorable rambunctious over time acceptance speech the year before, Basinger is in a state of shock at winning and produced one of the funnest thank you speeches in Academy history, she thanked everyone she ever met in her entire life. She then goes on to thank her director Curtis Hanson, her former husband Alec Baldwin, and her newborn baby Ireland. She ends the acceptance speech by dedicating it to her father who had passed away.

8. Kathryn Bigelow wins Best Directing…

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Director Kathryn Bigelow made history with her Oscar win at the 82nd Academy Awards when she won for Best Directing in 2010. She became the first woman to receive an Academy Award for Best Director for The Hurt Locker. She was the fourth woman in history to be nominated for the honor, and only the second American woman. A competitor in the category was her ex-husband, James Cameron, who directed the sci-fi film Avatar.

7. Cuba Gooding Jr. wins Best Supporting Actor…

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Cuba Gooding Jr. winning his Oscar for Best Supporting Actor for his role in Jerry Maguire during the 69th Academy Awards in 1997, was a truly memorable moment. The awards were held in the Shrine Auditorium. When Gooding Jr. won he was elated and overly excited while provided the Academy with a historic moment of what to do when you go over time and just enjoy the gravity of the moment. He literally jumped for joy as he left the stage with his Oscar, but not before thanking his wife, as Tom Cruise reminded him before the ceremony, he also thanked Cruise telling him “I love you brother!” It was one of the purest responses to winning in Academy Award history.

6. Aaliyah performs at the Academy Awards…

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Aaliyah‘s performance at the 70th Academy Awards in 1998 was a meaningful achievement in her career, she had mainstreamed her effort as a young musician to a national audience, by being asked to be sing the song “Journey to the Past” for the animated film Anastasia at the ceremony, the song was nominated for Best Original Song at the Oscars. She performed that night to a nationwide audience viewing, seemingly nervous but flawless in her performance, the same year she performed she was in good company, as Celine Dion was also there to perform the Original Song winner that night, “My Heart Will Go On” from the film Titanic. This career defining moment would live on in her fans hearts after she tragically passed away in August 2001 after a plane crash took her life.

5. Ben Affleck and Matt Damon win Best Original Screenplay…

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Ben Affleck and Matt Damon winning an Oscar for Best Original Screenplay for co-writing Good Will Hunting at the 70th Academy Awards in 1998 was a personal favorite of mine. I had dreams of screenwriting and had loved the film and to see these two young guys winning the award, gave me hope to pursue writing in any shape or form. They were so overjoyed, surprised and so funny when accepting their Oscar, and I felt that for them, even as a teenager. The award was presented by another generations “Ben and Matt,” Jack Lemmon and Walter Matthau, and upon announcing they had won Lemmon screamed their names and cheered in celebration, he was genuinely happy for them and I loved that moment. Affleck had also just become the youngest writer to ever win an Oscar for screenwriting, he was 25 years old, and still holds that record to this day.

4. Leonardo DiCaprio finally wins Best Actor…

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Leonardo DiCaprio, winning Best Actor for The Revenant at the 88th Academy Awards on February 28, 2016 was a long time coming. After years of being nominated for Best Actor six times and not winning, as well as being snubbed in other roles where it was felt he deserved a nomination, DiCaprio finally won Best Actor in 2016 for his film that included a scene where he climbed inside the carcass of a dead horse to survive the harsh winter weather was the film that finally got him the recognition his peers felt he deserved. One of those peers was his long time friend and co-star in Titanic, Kate Winslet, who was also nominated that night, and gets up to congratulate him for finally winning.

3. Envelopegate

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In one of the wildest moments in recent history at the Oscars, the craziest most emotionally filled wild moment was “Envelopegate,” the infamous wrong Best Picture was announced and realized on stage in real time with five minutes left the broadcast. The wild moment took place at the 89th Academy Awards when Faye Dunaway and Warren Beatty, co-stars in the 1967 film, Bonnie and Clyde, were presenting the last award of the evening, Best Picture. Dunaway announces the film La La Land as Best Picture, everyone cheers as they do for the big award of the night, and the producer Jordan Horowitz proceeds to the stage with the cast and crew to accept the award, its only when he’s handed the envelope traditionally given the the winner, and reads it, the Best Picture winner was Moonlight. He discovers this in real time while accepting confers with Dunaway and Beatty, even host Jimmy Kimmel comes into the fray of the chaos that has now ensued on stage, while everyone in the audience is jaw dropped watching not understanding what is going on. Horowitz holds up the envelope to reveal the real winner, and it takes a few minutes for everyone in the room to realize what’s going on, the cast of Moonlight rushes to the stage in a state of shock with Director Barry Jenkins, and the producers of the film. They take it all in while accepting the Oscar and giving their thanks, trying to beat the clock for the end of the three hour ceremony. Kimmel returns to the stage, in shock himself at what has just happened, makes a joke about it and then ends the night and broadcast. Beatty claimed he was given the wrong envelope, which turned out to be true, but due to the writing being so small he did not catch the mistake until after the presentation. The following year the envelope writing was made large and with bold print, so as not to ever re-live “Envelopegate” again.

2. Robin Williams wins Best Supporting Actor..

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Robin Williams winning the Best Supporting Actor Oscar for his role as Dr. Sean Maguire in Good Will Hunting at the 70th Academy Awards is by far my favorite of all Oscar moments. I was such a fan of his work in comedy, and as an actor, and he had pivoted into dramatic acting, and he was really good at it. This win for him solidified the bold move he had taken in his career and it’s one of his best roles in his career. What I found most moving about the moment was that his best friend of decades, Billy Crystal was hosting the Oscars that year, so when Williams wins and is shocked and excited at the same time, while he’s giving his acceptance speech the camera pans to Crystal who is crying tears of joy while smiling and clapping from the side of the stage. But the moment of all moments for me in his win, when Robin walks off stage and sees Billy there, he runs to him let’s out this profound sound of excited relief while he embraces his best friend in a hug so happy that he was there to share in the moment and history with him. This will remain a bittersweet moment, and one of my favorite moments to remember Robin Williams, since Robin took his own life on August 11, 2014 after experiencing depression, anxiety, and increasing paranoia related to a Parkinson’s Diagnosis. His autopsy found “diffuse Lewy body disease” and Lewy body dementia professionals said his symptoms were consistent with dementia with Lewy bodies. 

1. Will Smith Slaps Chris Rock…

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The slap heard around the world. At the 94th Academy Awards, Chris Rock was the presenter for Best Documentary Feature, and Will Smith was in the audience nominated for Best Actor for his role as Richard Williams in King Richard. Rock proceeded to make a joke about the nominees in front of him before announcing the winner, and as he mentions Smith, he notes that his wife is there with him, Jada Pinkett Smith, and references her bald head by saying he can’t wait to see her in G.I Jane 2. Well, let’s just say Will Smith wasn’t happy, apparently Smith‘s wife was still upset with Chris Rock over a joke he made about her when he hosted the 88th Academy Awards, and her clearly uncomfortable look as a result of the joke, led Smith to get up from his seat and walks up onstage and slaps Rock across the face. He walked back to his seat as people in attendance assumed this was a skit, and realize it was not, as Smith gets back to his seat and screams up to Rock, “keep my wife’s name out of your fucking mouth!” As the live telecast is still going on, Rock looks shocked as he finally announces the winner of the Oscar. Smith ultimately won the Oscar that night, but was banned from the ceremony for ten years, and gave up his membership to the Academy of Motion Pictures Arts and Sciences Board that allows him amoung many things, to vote for the nominees every year.

Based on “My Top Ten Oscar Moments” list above, I would have to say my favorite year for the Oscars were the 70th Academy Awards, without a doubt the 1997 Oscars were my favorite, and I love them all, but that year sticks out the most when it comes to my memory. There were so many other moments in Academy history but as usual on my blog I stuck to the top ten of those moments. As we head into the 96th Academy Awards this Sunday hosted for the fourth time by Jimmy Kimmel, I can not wait to see what new moments will be added to the cannon of Academy moments, as well as the new winners that will be added to the list of Oscar winners. I hope you found this list a nice ride down Oscar memory lane and don’t forget to tune into the Oscars at their new time, 7:00 P.M., on March 10, 2024!

See you at the Oscars!