Navigating Hollywood, Episode 5: Allen Wolf, Hollywood’s Biggest Night, Transcript

The original post for this episode can be found here.

Allen Wolf: Welcome to the Navigating Hollywood podcast. My name is Allen Wolf, and I’m a filmmaker, author, and game creator. Today, we’re talking about Hollywood’s biggest night. Notice, I’m not calling this our official Oscar® show. Why is that? Well, the words Oscar®, Oscars®®, Academy Award®, Academy Awards®, Oscar Night®, and A.M.P.S.® are protected by copyright and trademark laws, so you cannot create a show called the Oscar® show without written permission from the Academy. And they have made it very clear that they only will be posting shows that they have made that have those words in the title. So instead, we’re calling this Hollywood’s Biggest Night, which it is if you work in movies or, as I like to say, “Motion Pictures.”

I’m going to share with you some surprising facts and trivia about the Academy Awards®, and I’ll also share my own experience being an Oscar® best man. If you don’t know what that is, you’ll want to stay tuned to hear my story. If you’re listening to the podcast, you can’t see me, but I am dressed up in a tuxedo. At least my top half. This is also Hollywood’s fanciest night of the year, so why not?

And why do I even own a tuxedo? Well, I’ve been to several movie premieres dressed like this during the Cannes Film Festival. When you’re there, going to one of the premieres, they do require you to wear a tuxedo at all times. So, I also have two different bow ties. A real bow tie and the one I’m wearing – the clip-on bow tie. Usually, I start with the real bow tie, but if I can’t figure it out or if I just get super frustrated, I go with this, my emergency backup.

I’m also going to be giving away prizes for you, our listeners. So stay tuned. I’m going to ask a question at the end of our time about something I mentioned during the podcast. Then I’m going to send a copy of my gamebook, You’re Pulling My Leg, to the first 20 people who answer my question.

Now Oscar® night is Hollywood’s biggest night of the year, if you work in movies, and that’s because of what the Oscar® represent – the highest achievement for a motion picture voted on by your peers. The Academy Awards® started in 1929 when they handed out their first awards at a dinner party for about 250 people at the blossom room of the Roosevelt Hotel in Hollywood. If you’ve ever been to downtown Hollywood to the Mann Theater, further down the street from there is the Roosevelt Hotel. They have a little plaque outside the room that says this is where the Academy Awards® began.

The head of the MGM Film Studio, Louis B. Mayer, created the Academy in May of 1927 as a non-profit organization dedicated to the advancement and improvement of the film industry. This is why you not only see Oscars® given out for achievement in film, but also they give out Oscars® for technical achievements that help advance the filmmaking process as well.

Let’s talk about the very first Oscars® show. The winners of the first Oscars® in that ballroom were announced before the award ceremony itself. So no one who showed up did not know they were going to win. They were winners of the Oscar®.

It was first televised in 1953, and the ceremony has now seen in more than 200 countries now, I think the Oscars® are also an amazing time capsule. I love going on YouTube and watching the opening ceremonies of the Oscars® throughout the years because it really helps put things into perspective. I know there is a lot of adoration for people that you see on the Oscars®, especially the actors, and as you look at the past Academy Award® presentations, you realize, okay, I don’t know who a lot of these people are or you look at people and you realize, wow, their lives have not moved in a good direction. That person has been arrested, that person’s life ended prematurely. Or you see someone else and you see that person has actually made a huge difference in the world. So it actually helps give a little perspective as you take a journey back and look at the early Oscar® shows

Well, there is a huge difference between the ages of the nominees.The youngest ever Oscar® winner for a competitive acting award was Tatum O’Neal. She was 10 years old when she won for Paper Moon in 1973. I don’t know if you’ve seen that movie. My parents showed it to me when I was young my sister and I really enjoyed it a really fun movie. The oldest winner was Christopher Plummer, who won it at age 82.

Before that, the oldest person to win an Oscar® was actually Jessica Tandy at the ripe old age of 81. She won the Best Actress award for her part in Driving Miss Daisy. Christopher Plummer also holds the record for oldest acting nominee. He was 88 years old for All The Money in the World and believe it or not, his role was shot in eight days. They actually had to replace the role that Kevin Spacey had originally and then, funny enough, Christopher Plummer was nominated for an Oscar® for his part in that film.

The oldest ever Oscar® winner in any category was screenwriter James Ivory at 89 years old. So if you’ve been working at your craft for a long time, hoping someday you’ll be recognized by The Academy of Motion Picture Arts and Sciences, well, just hang in there, because your day might be coming up.

At the 2013 Oscars®, two actresses made history as the youngest and oldest nominees ever in the actress in a leading role category Quvenzhané Wallis who was nine years old for Beasts of the Southern Wild and Emanuelle Riva who was 85 for Amour. So hang in there. Keep going. Your time is coming up.

Did you know Oscar® winners don’t really own their statues? Upon receiving the trophies, winners actually have to sign an agreement that says if they ever want to sell their statuettes or get rid of them, they have to first offer them to the Academy for $1. And if they refuse, they can’t keep the trophy.

Now this rule started after 1950. So every once in a while, older Oscars® actually come up for sale that were given before 1950. But only if the person who won the Oscar® was no longer a member after 1950 because if they were, they agreed to the Academy’s bylaws, which clearly states that anyone who would no longer like the keep their statue would have to sell it back to the Academy for one dollar.

Now Michael Jackson paid 1.54 million in 1999 to own producer David. Selznick’s Best Picture Oscar® for the 1939 classic Gone With the Wind but funny enough after spending all that money for that Oscar®, no one can find it after he died in 2009. The executor of his estate says they can’t find the Statue. Can you believe that? 1.54 million dollars. They’re probably better things that money could have been spent on. Well Steven Spielberg bought Betty Davis’s Oscar® for $578,000 and in 2001 donated it back to the Academy. And then he bought Clark Gable’s 1930 for best actor Oscar® for It Happened One Night for the price of $550,000 in 1996 and gave that to the Academy as well. Very generous man.

Peter O’Toole holds the record for having the most best actor nominations without winning a single one. However, in 2003, at the age of 70, they said, you know what? We want to give you an honorary Oscar® for all the work you’ve done. At first, he didn’t want it but then he changed his mind and said, okay. So eventually he did get an Oscar®.

Who has the most acting nominations and has never won? Richard Burton and Glenn Close. I know a lot of people thought last year in 2020 was going to break her record, but it didn’t. And I think I’m betting she’ll be nominated again.

What film was the first color movie to be an Oscar® winner? That was Gone with the Wind.

Who has won the most Oscars® ever? Well, that would be Walt Disney. He has been nominated for 64 awards and he has 26 now, believe or not. He was nominated for one Oscar® every year between the years 1942 and 1963. So I guess when he started a year, he thought this is the yea I’m going to be nominated for another Oscar®.

Who is the second most nominated person? It is the composer and, frankly, one of my favorite composers John Williams. He has been nominated 47 times and counting.

Only three films have ever won all five Oscars® for best film actor, actress, directing, and writing. They are It Happened One Night, One Flew Over the Cuckoo’s Nest, and The Silence of the Lambs.

Who is the actress with the most Oscars®? Well, that would be Katharine Hepburn as she has won four Best Actress Oscars® during her career.

Now Clint Eastwood has the most Oscars®, but he did not win all of those for acting. Actually, he didn’t win any of those for acting. He won two Oscars® for Best Directing and two Oscars® for Best Picture.

Who has won the most Best Actor awards? Well that would be Daniel Day-Lewis. He won for My Left Foot, There Will Be Blood, and Lincoln. However, Jack Nicholson has also won three Oscars® two of them were for best actor and one was for best supporting actor.

Who was the first female Best Director winner? That would be Kathryn Bigelow. She won for The Hurt Locker Don’t know if you’ve seen that, but I remember when it was nominated. Avatar was also nominated the same year. I remember during the ceremony, they would frequently show James Cameron and Kathryn Bigelow in the same shot because they were formerly married. They sat her behind him and they were just constantly go to the two of them to create tension. To make us think, who’s gonna win? And ultimately she prevailed.

Until 2021, she was only the fourth woman to ever receive a nomination. But in 2021, two more women were nominated for best director. Chloe Zhao for Nomadland and Emerald Fennell for Promising Young Woman. So congrats to those women.

And the most expensive winner ever, you can probably guess because I mentioned the title already. That was Avatar. Guess what the budget was? 280 million dollars. That’s a lot of money. It didn’t win Best Picture or Best Director, but you know, it picked up some awards for Art Direction, Cinematography, and Visual Effects.

Let’s talk about some Oscar®-winning families. Well, several couples have won Oscars®. But only one Hollywood family can claim to truly be Oscar®-winning. That would be the Minnelli family. Liza Minnelli won best actress for Cabaret in 1973. She is the daughter of Vincente Minnelli, who won best director and 1959 for Gigi. She is also the daughter of Judy Garland, who received a miniature Juvenile Award in 1948.

Now who directed his own father and his own daughter to an Oscar® win? That is John Huston. He directed his father Walter Huston to an Oscar® for The Treasure of the Sierra Madre, for which he actually also won Best Director. He also directed his daughter Angelica Huston who won an Oscar® for Prizzi’s Honor. Amazing.

Now, who has the most memorable Oscar® speech? Do any come to mind if you’re a fan of the Oscars®? For me, I think of Gwyneth Paltrow’s very tearful speech she gave where she talked about her father. But I especially remember Roberto Benigni stepping on the chairs in front of him to accept his Oscar® for Life is Beautiful. That was a pretty amazing moment. But the longest speech goes to actress Greer Garson who talked for seven minutes when she won the award for Best Supporting Actress in 1934.

Now the award itself is gold-plated except during World War II, they handed out plaster trophies that they painted and later said you can exchange them. It might be fun actually to though have that one because there was a shortage of metal during the war.

The Oscar® award costs $500 to make. It weighs around eight and a half pounds and the company who makes it as based in Chicago. RS Owens. They start making those Oscars® a year in advance of the show.

So the name of the trophy is actually the Academy Award of Merit but it’s known as the Oscar®. No one really knows why. But there is a theory, a theory that there was a librarian who eventually became the executive director for the Academy, and she said, you know what this kind of looks like my uncle named Oscar. So I guess the nickname stuck and eventually became the nickname officially associate with the trophy.

Starting in 1939, Peter Finch and Heath Ledger are the only actors to be awarded an Oscar® after they died. Ledger’s Oscar® was gifted to his young daughter Matilda. In 2021, Chadwick Boseman might join them.

I know a lot of people were shocked and saddened by the death of Chadwick Boseman. It brought up a lot of questions about what life is all about and what happens after we die. If those are questions you’re wondering about I would suggestyou check out the courses Navigating Hollywood has to offer, their Marriage Courses and the Alpha Course where you can explore life’s big questions.

You can find out more about those by going to The courses are for people who work in entertainment, and they are complimentary. If you use the invitation code podcast. Again, go to and use the code podcast.

Who has been nominated for the most Oscars®? That would be Meryl Streep. She has been nominated for a record 21 Academy Awards®, winning three Best Actress Oscars®. Her most recent was for The Iron Lady In 2011. Jack Nicholson is the most nominated male actor, having received 12 Oscar® nominations and all that started with his 1969 movie Easy Rider.

There are three films that have won 11 Oscars®. Those are can you guess them then?

Ben-Hur, Titanic, and Lord of the Rings: Return of the King. Now with that last film, Lord of the Rings, they actually won every award for which they were nominated. Isn’t that incredible?

Now, why are the names of the winners so secret? Let me tell you who to blame. The LA Times In 1940, the LA Times broke the Academy’s embargo and published the names of all the Oscar® winners before the ceremony. So after that, the Academy said, you know what we’re going to introduce a sealed envelope, and they’re still doing that today.

Bob Hope was the host who hosted the most. He actually hosted 19 times, the most frequent Oscar® host ever.

After the 2002 ceremony, the show ran for an astounding, can you believe this, 4 hours and 23 minutes and the Academy said, you know what we’re going to get 45 seconds to thank the people you love. After that, the orchestra is going to start playing you off. So they’ve continued that to this day. I have noticed, though during the end of the night, when you get to some of the more significant awards, that you start seeing that they’re taking a lot longer with your time.

The record for the shortest acceptance speech is shared by two people: Alfred Hitchcock and William Holden, they both simply said, thank you.

You know who wore the most expensive dress in Oscar® history? That would be Jennifer Lawrence. Her bluish-pink ball gown that she wore in 2013 was valued at, ready for it, 4 million dollars. Yeah, 4 million dollars. It was lent to her. I’m not sure it was it lined with gold and diamonds like what made that 4 million dollars, maybe we’ll never know.

Now, what country has won the most International Film Oscars®? That would be Italy. Believe it or not, they have won 10 times. Incredible. No film has ever won the quartet of acting Oscars®. That would be Best Actor, Best Actress, Best Supporting Actor, and Best Supporting Actress. The closest that anyone has come is 1950’s A Streetcar Named Desire. The only other film that came close was Network. But then, you know, Ned Beatty lost out in the Best Supporting Actor category.

Let’s talk about the Oscar® itself. It is plated and 24 karat gold. It’s made of solid bronze, weighs 8 and 1/2 pounds and stands 13 and a half inches tall. And as I said, during World War II, it was not made of metal. It was instead painted plaster.

Only two sequels have ever won Best Picture. That would be the Godfather Part 2 and the Lord of the Rings: The Return of the King.

The Oscar® ceremony has never been cancelled. Can you believe that? But it has been put off four times. The first was because of flooding in 1938. They pushed it by week. Then when Dr. Martin Luther King Jr. was assassinated, they postponed it by two days. And when former President Ronald Reagan was almost assassinated, they pushed it off for 24 hours. Then, of course, we’re living history people, in 2021 is delayed for two months because of covid. Thanks Covid.

The person who has lost the most in Oscar® history happens to be Kevin O’Connell. He’s a sound re-recording engineer and he’s been nominated 20 times since 1983’s Terms of Endearment, but he’s he hasn’t won. Poor guy. I wish they would have maybe given him an honorary Oscar®. That would have been nice.

I would say the strangest recipient of the Oscar® would go to a propaganda movie that happened during 1941. It was a documentary, actually docudrama, called Target for Tonight. Amazing. I wonder if the person who made that ever thought, I’m going to win an Oscar® for my propaganda film. They did.

Now which films earned the most Oscar® nominations? That would be All About Eve Titanic and La La Land, and they’re tied for the most nominations at 14 each. All About Eve ultimately won six, Titanic won 11 and La La Land won 6. But while All About Eve and Titanic both won best picture well, La La Land was the most nominated film ever to lose the top prize. Sad.

Six Oscar® wins have actually been tied. The most famous is perhaps the tie for best actress between Katharine Hepburn for Lion in Winter and Barbra Streisand for Funny Girl. Now Hepburn didn’t actually show up that night so Streisand went up to accept her Oscar® and if you’ve ever seen the footage from that ceremony, it’s when she looked at it and said, hello gorgeous.

Which film won best picture after the wrong winner was announced? This is much more recently. So maybe you saw this. I did. Really crazy. Could not believe it. It was when Warren Beatty and Faye Dunaway accidentally read the wrong winner due to them having the wrong envelope. It was two and a half minutes later when Moonlight then took the stage and ended up winning best picture. That was a crazy situation. I remember seeing the producer, one of the producers, of La La Land, be the one who said, “Actually we didn’t win. Moonlight won.” And he handed the Oscar® to the winner. His name is Jordan Horowitz. I met him later and I said, “Jordan, what was going on in your mind? I was so impressed by how you took charge and handed the Oscar® over to the winners.” And he said, “You know what? I just went into producer mode. Everything was on fire. Someone had to take charge. So I stepped up to the plate.” And he did. It’s really kind of fun to watch his character come out in that moment.

Now which movie earned the most nominations but didn’t actually win any? There’s a tie. The Turning Point and The Color Purple. They each went into the Oscars® with 11 nominations and didn’t win any. I’m sure those were very, very disappointing nights. “Oh my gosh, we have 11 nominations. We’re going to win something.” Nope. Not good.

Now what about how many times has Alfred Hitchcock won Best Director? Take a guess. Zero. That’s right. Unbelievably, someone who’s perhaps known as the greatest director of all time has never won a directing prize. But don’t feel totally bad for him. He did win for his movie Rebecca. He won Best Picture for Rebecca. That was the first film he shot in America.

Which movie first won the Oscar® for Best Animated Film? If you said Beauty and the Beast you are incorrect. That was actually the first animated film to be nominated for Best Picture, but then they created a whole separate category for Best Animated Film and the first winner was Shrek. Before that, Snow White and the Seven Dwarfs won an honorary Oscar® and seven little statuettes for their achievement for what they achieved and their movie and other films that Disney created also won Oscars® and music categories before that. But Shrek was the first official film to win Best Animated Film.

Now, which Broadway star got jilted and then got revenge on the Oscar® stage? Well, Julie Andrews won a Tony Award for portraying Eliza Doolittle on Broadway in My Fair Lady, but they decided, you know what? She’s just not famous enough to be in the movie. So instead they put in Audrey Hepburn. Audrey Hepburn ended up being nominated for her role. But who else is nominated? Julie Andrews. She was nominated for Best Actress in Mary Poppins. And who won? That would be Julie Andrews. So there you go. I bet they wished they had put her in both roles. Well, then maybe she wouldn’t have won because she would have been competing with herself. Who knows now.

Who won Best Picture between Gandhi and ET the Extra-Terrestrial? it was Gandhi and later Richard Attenborough who directed Gandhi said, you know what? I actually think ET was the better movie. I wish it had won. Wild. Well, he eventually made it up to Spielberg by starring in Jurassic Park.

Who else was in Jurassic Park? Laura Dern and her dad was nominated twice for an Oscar®, but it was Laura who was the first to bring home an Oscar® statuette.

Parasite was the first South Korean film nominated for best International Feature Film as well as for Best Picture and Best Director.

The largest US TV audience for an Oscar® show was in 1998. 52.2 million people watched and what was the movie that won best picture that year? It was Titanic.

Now, the least-watched Oscars® was very recently. Last year. 23.6 million viewers. It still sounds like a hefty number but it is the lowest number ever. It was 20% less than the year before. Many people are thinking that 2021 will be the lowest show, and I know the producers are doing everything they can to make sure that doesn’t happen. And I don’t know why. Is it that people care less about the Oscars®? Does Hollywood seem to politicalized? Too out of touch? You tell me. Go on our Instagram page our Facebook page. It’s at Navigating Hollywood. Tell me what you think. I’d love to know.

The closest I’ve ever come to attending the Oscars® was when a friend of mine asked me to be his Oscar® best man, and I remember saying like what’s an Oscar® best man? And he said, you know what? It’s the guy he’s like right beside me on Oscar® night helping me to get ready. His wife is going to have her friends next to her helping her to get ready. It’s a whole thing, and there’s a lot of prep that goes into building to that night. There’s a whole campaign season and a lot of stress.

I remember that one of the issues they are working through is that his wife was constantly needing a different gown for each night. These are first world problems, but I know she needed a new gown for every show that she went to and they had to keep getting people to loan them gowns.

Well, his film was nominated. It was best live-action short nomination and it’s called (listen to the podcast) and so I said, yeah, I’d love to be there. So I went over and I helped him tie his bowtie. We didn’t use the emergency bowtie that I use sometimes, and I gave him a shampoo bottle so he could practice his speech if he won and we actually even came up with these blue ribbons that he asked the other nominations to where to bring attention to human trafficking and they did. Amazing. That’s an issue that’s near and dear to my heart.

And then I wrote Gregg two letters. One was a letter that I wanted him to open if he won and the other letter was one he would open if he lost. And when I was writing a letter to him that he would read if he won, you know, I remind him that ultimately what mattered was not that he won the Oscar® What mattered was that God loved him no matter what. God loves him unconditionally and I thought that would help give him some perspective.

I know two of our recent guests talked about how important it was for them to be grounded in the reality of how much God loves them in order to survive the roller coaster of Hollywood. I thought it’d be good to remind him of that too. But then it’s funny when I wrote him the letter that he would read if he lost, I realized I was writing him the exact same message. What really matters is not what his peers think of him, but what God thinks of him and God loves him unconditionally, and God loves all of us unconditionally. So no matter where you are right now, whatever ups and downs you’re experiencing, or maybe you’re feeling crushed by something or something, someone said something. Remember, God loves you unconditionally. Well, he ended up not getting the Oscar®, but he thanked me for being with him on his journey, and I love being by his side.

Well, thank you for being with me on this journey today through the history of the Oscars®. And now for our contest, I’m going to be giving away 20 copies of my game book, which is called You’re Pulling My Leg. It’s a game that helps people get to know each other and build relationships. So here’s the question (see podcast). If you know it, email me the answer at info(at) Again, that’s

The first 20 people who email me will win the book. If you don’t hear back from me, it means all the books have been given away. So congratulations in advance.

Thank you for tuning in to our special show about Hollywood’s Biggest Night. Navigating Hollywood is dedicated to helping people who work in entertainment to have relationally and spiritually holistic lives. Check out the courses that are available at and again use the word “podcast” to register for a complimentary course. Please follow us and leave us a review so others can discover this podcast. You can find our other shows, transcripts, links, and more at Thank you again for listening, and I look forward to being with you next time.