Why Leonardo DiCaprio Finally Won His Oscar

On the night of February 28th, 2016, there was a lot of suspense at the 88th Academy Awards. Best Picture could have gone a few different ways. You had Spotlight, you had The Revenant, you had at least three films in that category that had a chance to win. In Best Director, it came down to Alejandro G. Iñárritu and George Miller. Iñárritu was the favorite to win, but he had just won the year before for Birdman, so were they going to give him another gold trophy just one year later? That was the question. And then you had Best Supporting Actor and Best Supporting Actress, and those categories could have gone a number of ways as well. Best Supporting Actor looked to be going to Sylvester Stallone for Creed. He had won a couple key prizes. But then you had Mark Rylance breathing down his neck for Bridge of Spies. He had won at BAFTA, and that film was in Best Picture. Creed was not, so that was kind of a toss-up. Best Supporting Actress could have gone to Kate Winslet for Steve Jobs. She won at the Golden Globes and at BAFTA. But then you also had Alicia Vikander for The Danish Girl. She won at SAG, and she was also in Ex Machina the same year. Like, she was really great in two different films. So that race was also suspenseful, like a lot to talk about there. I have made videos for the channel in recent months on Best Supporting Actor and Best Supporting Actress 2015. So yeah, there was a lot of excitement that night, and going into the ceremony, I wasn't too sure about my predictions. I wasn't overly confident, but there were two top categories that were basically 100% guaranteed. Best Actress was going to Brie Larson for Room. She had swept the season. No one could take her down, so that was happening. And then probably the biggest foregone conclusion of that entire night was that Leonardo DiCaprio was finally winning his Academy Award for The Revenant. And in today's video, with one battle after another in theaters, it's time to go back and talk about why. Why was Leonardo DiCaprio such an obvious win that year in Best Actor? Why couldn't anyone else take him down? What was DiCaprio's Oscar journey on the way to 2015? And what were the main reasons it was so obvious he was going to be victorious that night? Hey guys, it's Brian. Welcome to the Awards Contender. I have a new Oscar race retrospective for you today. I've never talked in depth on this channel ever about Leonardo DiCaprio. Like, obviously his name comes up in things here and there, top 10 videos and stuff. But I've never really talked about DiCaprio for an entire video, and so I thought it was finally time to dive into his Oscar win for The Revenant, talk about his journey to the Oscars before and after. It's everything DiCaprio on the Awards Contender today, and so let's begin by talking about that Best Actor race for 2015. Who was his competition? Was there any competition? There wasn't much. If you remember back to that year, like, DiCaprio was winning that thing, and we're going to get into it. But yeah, let's break down the other four nominees and Best Actor for 2015, starting with Eddie Redmayne for The Danish Girl. You should have been there. How could I? Look at me. Not everything is about you. So this is an Oscar nomination that hasn't aged very well, right? That did not need to happen. Like, we didn't have a ton of contenders in Best Actor that year. That was part of the problem. We had to fill up the category, right? Like, Johnny Depp for Black Mass was getting into a few places. You had Will Smith in Concussion. He got in at the Golden Globes. That looked to be a potential Oscar play for him, but that didn't pan out. You also had Jacob Tremblay in Room, who got into Best Supporting Actor at SAG. I think Jacob Tremblay is a lead actor in that movie. I don't care how young he is. I think he would have been an inspired Oscar nomination for the ages in Best Actor for Room. That would have been amazing. It would have been much better than Eddie Redmayne in The Danish Girl, where he plays a transgender character named Lily in this period drama, also starring Alicia Vikander, of course, who won the Oscar for Best Supporting Actress, directed by Tom Hooper. That thing had Oscars written all over it before the cameras even started rolling, right? Like, this was obviously going to be a prestige period film that would be an Oscars player, and it didn't get into Picture and Director and stuff. It got into two acting categories. That was basically as good as it can do because the movie is just okay. I watched it once. You know, it's not a bad film, but it doesn't really stay with you. It's obviously about very important subject matter, but the casting of Eddie Redmayne in that role was problematic, to say the least, and I don't know. I just I don't think this Oscar nomination for Redmayne needed to happen, especially because he just won the year before in a tight Best Actor race with Michael Keaton for Birdman. Redmayne pulled it off for The Theory of Everything. So, like, he just got one. Why did he have to come back for this film, this performance? I didn't really see it. Next up is Bryan Cranston for Trumbo. You have no idea what you could lose. Oh, please. My career, the First Amendment, our country. Am I missing anything? So, this is something that might help you win, like, a trivia round somewhere. If someone asks, like, what film did Bryan Cranston receive an Academy Award nomination for, you're going to remember this answer, right? Trumbo, 2015. Because, kind of like The Danish Girl, that was a perfectly fine film. Like, it's not bad. It's not great. It's just kind of so-so. It's there. It had a good cast and an interesting story about how, in the 1940s, top Hollywood screenwriter Dalton Trumbo was blacklisted in the industry for his political beliefs. It's got a good ensemble cast. Helen Mirren came very close to getting an Oscar nomination for Best Supporting Actress. As Hedda Hopper in that film, she got into a few places, and I do think was, like, in sixth place, potentially, to get into Best Supporting Actress at the Oscars. Bryan Cranston made it into Best Actor in kind of a limited field, right? He's the only nominee for that movie. It did not get into any technical category, nothing else. And I do think that's the reason he never had a shot to win. Like, even in a field where there wasn't a clear frontrunner, like, Cranston was always going to be in fourth or fifth place. He's very good in that film. He transforms physically into Dalton Trumbo. This is not a bad Oscar nomination. This one can stay. I really like him in that. And I'm very happy that Cranston has an Academy Award nomination. I think that's great. But yeah, he was definitely just happy to be there. Michael Fassbender, Steve Jobs. So I would put Fassbender in third place here, mostly because he was on his second Oscar nomination. He had been nominated two years before in Supporting Actor for 12 Years a Slave. And Fassbender is excellent in Steve Jobs, directed by Danny Boyle, written by Aaron Sorkin. He shares the screen with some wonderful actors, including Kate Winslet, who I said before, did come very close to winning Best Supporting Actress at the Oscars, I think. It's a physical transformation for Fassbender. He definitely becomes Steve Jobs, not just in one period of the man's life, but in three, right? It bounces around to different time periods for him. And it's a really fantastic performance. I think the problem is the movie wasn't really well received by critics, especially by audiences. This movie flopped at the box office. I think I told this story in the video about Kate Winslet versus Alicia Vikander. Like, this movie in my town was basically out of theaters on the third weekend. Like, it didn't make an impact at the box office at all. And I do think that was a problem. If this had been an even, like, medium-sized hit, and it stuck around in November and December and stuff, like, maybe Fassbender could have been slightly more competitive, but no. I think in a different year, he might have been, like, closer to second place, maybe. Not really first. I don't think that was ever going to happen. He knew that night at the Oscars in early 2016, he was going to be applauding from his seat, Matt Damon, the Martian. So, as I'm going to talk about in this video, there wasn't really competition. DiCaprio had this in the bag. If you were going to argue, was there somebody who was, like, somewhat close to DiCaprio? Like, was there anybody who could, like, like, maybe overtake him? The only person you could talk about was Matt Damon for The Martian. He won at the Golden Globes. He got in basically everywhere throughout the season. The Martian got into Best Picture at the Oscars and was a very beloved movie that season. It did really well at the box office. It's very funny and dramatic and emotional, very exciting at the end. And it's one of Matt Damon's most appealing performances. Damon is so great as an astronaut named Mark who becomes stranded on Mars and is doing everything he can to stay alive as rescue missions are put in place to bring him back home. So, like, if DiCaprio is not in the conversation, if The Revenant comes out in 2016, let's say, or something, Matt Damon would have won this in a landslide, I think. I think this would have been Matt Damon's year. Of course, he had already won an Oscar for Good Will Hunting 1997, but that was for its screenplay, of course, co-written with Ben Affleck. Matt Damon, still to this day, has never won an Oscar for acting. The closest he's ever come was for The Martian 2015. Like, he had no shot for Invictus. So, in terms of acting at the Oscars, Matt Damon, the only one I would say he was, like, in second place for was for The Martian. But sadly for Damon, this was DiCaprio's year. And by the night of the 88th Academy Awards, when we got to Best Actor, all four of these other guys who were sitting in the auditorium, like, hearing their name called, along with everybody else sitting there, everybody at home watching the telecast, we all knew this Oscar win for Best Actor that night was going to Leonardo DiCaprio for The Revenant. Leonardo DiCaprio was so likely to win this that night, I think if he had lost, if it had gone to Matt Damon or someone else, it would have been the shocker of the decade. It probably would have been an even bigger shock than what happened the next year in Best Picture, Moonlight vs. La La Land. Everything that went down there was crazy and unexpected and bizarre and all of that. I still think DiCaprio losing for The Revenant would have been an even bigger shock in a way. His performance as a frontiersman named Hugh Glass in the 1820s was universally lauded by critics, by audiences, and with the film opening in limited release in December and then going wide in January. It was on everyone's minds, that award season. This didn't come out earlier in the year and had to build and the word of mouth and getting DiCaprio's name in all of the awards voters' minds or anything. As award season was heating up, the movie was opening wide and doing incredible box office. Everybody was seeing this film, talking about it. No matter what your feelings were at the time about The Revenant, everybody was discussing that film. How it was made, the performances, the direction, the cinematography. You know, January, February, March of 2016. The Revenant was everywhere and it's almost like DiCaprio knew. He knew this was his moment to finally win his Oscar. So what are the main reasons this was such a foregone conclusion? Why everybody in the whole freaking world knew come Oscars night this was DiCaprio's time? I've got five. I've got the five main reasons DiCaprio finally won his Academy Award. So the first two reasons are the most important. Like they are the pivotal reasons this happened. The first one was that he was very much overdue. He had an overdue narrative that year for The Revenant, unlike any we've seen really in the last 15 years. Everybody in the industry wanted to see DiCaprio win an Oscar. Hell, like just people at home, casual moviegoers. You know, you would say, oh, you know, Leonardo DiCaprio has never won an Oscar. And people be like, what? Like, how is that possible? He's so good every time out. He works with the best directors. He appears in one amazing film after another. For decades, he still has never won. And that overdue narrative in early 2016 kicked into high gear, whether it was being promoted or not. Everybody knew, okay, this year, it's time for DiCaprio. So what was his Oscar journey leading all the way up to 2015? There were highs and lows. You know, he got nominated a few times. He was snubbed a few times, very famously, I would say. Let's go back to the beginning, his breakthrough year of 1993. He's in This Boy's Life opposite Robert De Niro. And he's in What's Eating Gilbert Grape, where he just completely transforms in that film, immerses himself in the character. And even though he was really young at the time, everybody was like, holy ----, right? Like, who is this kid actor? Like, who is this guy? DiCaprio is absolutely phenomenal in What's Eating Gilbert Grape. He received a much-deserved Best Supporting Actor Oscar nomination. I think he was young enough at the time. The movie overall didn't do very well come award season, like in other categories. So I don't think he ever had a shot to win for that one. He was part of the club now, he was an Oscar nominee. And it was really exciting around that time to see where his career would go. His next play for Oscar, of course, was Titanic 1997, like one of the biggest movies of all time. And that film received a then-record, still a record to this day, tied with La La Land and All About Eve, 14 Oscar nominations. Titanic got into basically every category it could, except for Best Actor for DiCaprio. Arguably, like, the best thing about the entire film is the DiCaprio performance. He is frickin' amazing in that. He did not get in at the Oscars for Titanic, so that was kind of a snub. Because the movie was so crazy popular, it's like, okay, Kate Winslet gets into actress, like, why can't DiCaprio get into actor? That was kind of weird. 2002, he is snubbed again for two end-of-the-year Oscar-baity films, right? Catch Me If You Can by Steven Spielberg, which gets him in at the Globes, and Gangs of New York by Martin Scorsese, their first collaboration together. That film got 10 Oscar nominations, right? Including picture and director. But when it came to awards, DiCaprio was mostly overlooked that year again. His second Oscar nomination arrived 2004, The Aviator, right? That one had to happen. He's so great in that film. He is the entire show, there's a big ensemble cast, but it's all Howard Hughes all the time for three hours, and it's Martin Scorsese again, the film gets a new Best Picture, Best Director again, and so there DiCaprio is in Best Actor at the Oscars for the very first time. You could argue DiCaprio was in second place that year to win the Oscar because he won the Golden Globe Award for Best Actor in a Motion Picture Drama, and The Aviator got into a ton of categories at the Oscars. They clearly loved the film, so DiCaprio was in play there. But that was the year of Jamie Foxx and Ray, and he basically steamrolled the season. Nobody was beating Jamie Foxx that year, so DiCaprio had to settle for second place. He was also still pretty young, right? He had been in some big films like Titanic and Romeo and Juliet and some things. But in 2004-2005, he didn't quite have the overdue narrative yet. He was still kind of young, so he was going to have to wait, you know, do some more big films, and one of these years it was going to happen. In 2006, he receives his third Oscar nomination, this time in Best Actor for Blood Diamond and not The Departed, which was kind of a surprise that season. Obviously, The Departed went on to win Best Picture and Best Director, so if DiCaprio had been nominated for that film and not Blood Diamond, he probably would have had a better shot to finally win. But that was the year of Forrest Whitaker and The Last King of Scotland, and he also just swept the season for the most part, right? So he was pretty much guaranteed a victory that night. DiCaprio would not have arrived at that ceremony thinking he was going to win. 2008, he gives a great performance in Revolutionary Road, but that film comes up short on Oscar nominations morning, like it doesn't do very well. 2010, he's of course very good in Christopher Nolan's Inception. That film gets in at the Oscars, but it wasn't really looked at as an acting showcase, like something that would get an acting nomination. That was never really in the cards. 2011, he's in Clint Eastwood's J. Edgar, and he gets in at the Golden Globes, and it's sag, if I remember right. And there was talk, like maybe he could squeak in there for Best Actor at the Oscars, but that movie was not very well liked. I didn't much care for it. I was not sad when DiCaprio missed an Oscar morning for J. Edgar. In 2012, he's in Quentin Tarantino's Django Unchained, as a much different kind of character than he usually plays, like the villain. He is so memorable in Django Unchained. I remember walking out of that film on Christmas day thinking, man, this could win him the Oscar. This could be it. It'll be in Best Supporting Actor. It'll be so well deserved. He got in at the Globes, and I think that was it, right? Christoph Waltz won Best Supporting Actor at the Globes that year for the same film, Django Unchained, and then he went on to win the Oscar for Best Supporting Actor for that film, like DiCaprio just couldn't catch a break, right? He was doing really good work year after year, in oftentimes big films that made a lot of money at the box office, that did well with critics, and it just wasn't happening for him. But then in 2013, along came The Wolf of Wall Street, and if there was ever a film that got him really close to an Oscar win, it was that one from Martin Scorsese. That movie came out at the very end of the year, three hours of just absolute nuttiness. He gets to play everything in that movie. He's very funny at times. Some of the biggest laughs I had in a film that year was in the scene where he takes the Quaaludes and he's trying to get to his car. That scene is freaking hilarious. DiCaprio is not often thought as a Oh my god, he's so funny in that film in a variety of scenes. He's also very dramatic at times. He gets to play everything in that. He won the Golden Globe Award for Best Actor in a Motion Picture, Musical, or Comedy. He got in pretty much everywhere that season, but that was the year of the McConnaissance. Matthew McConaughey and Dallas Buyers Club, that was the performance pretty much everyone got in line with by the time of SAG and the Oscars. That was a foregone conclusion for 2013. It wasn't going to be DiCaprio for The Wolf of Wall Street, even on Oscars night, I was crossing my fingers. I was like, come on. That was the performance I wanted to win. I wanted DiCaprio to have an Academy Award, but of course it was always going to McConaughey. DiCaprio, he couldn't overcome that narrative. That comeback narrative for McConaughey was just everywhere that season. Even though The Wolf of Wall Street got into Best Picture and Best Director, it surprised in Best Supporting Actor for Jonah Hill, I remember that. Dallas Buyers Club also got into Best Picture. Jared Leto won Best Supporting Actor. It was just, that was a tricky situation. DiCaprio, I do think probably was semi-close, maybe not super close, but he was definitely in second place. And I remember when that Oscars telecast ended. I said, okay, the next time Leonardo DiCaprio receives another Oscar nomination, he is winning. He is 100% winning. He's not going to get another two or three nominations and go home empty-handed. The next time he's in a great film, he gets into the Oscars, likely in Best Actor, he is going to be victorious. And we didn't have to wait very long, right? We only had to wait two more years. I mean, pretty much right after he lost the Oscar for The Wolf of Wall Street, we were starting to hear about his next project, The Revenants. And with that director, with that cinematographer, that story that I was starting to hear things about, I was like, ooh, this could be DiCaprio's moment at the Oscars. Like long before I ever saw a still or a shot from the film or the trailer or anything, there was already buzz while that movie was being made that this could be a big awards contender, that DiCaprio might finally win an Oscar. The movie just had to be really good or great, you know, do well at the box office, like have a good release date. It was going to happen. So it was almost like pre-programmed, like months in advance, like going into the fall of 2015. I was like, there doesn't seem to be a frontrunner in Best Actor right now. It looks like as long as that film is amazing, DiCaprio might take it this year. And he did. He had an overdue narrative for the ages. One of the biggest overdue narratives we've seen in a long time. And so that is the number one reason why he won. The other huge reason, reason number two, was the lack of competition in the category. That was the other big reason why he took this. As I said before, Matt Damon for The Martian, that was the only performance in the category that like was in second place, you could argue, like was maybe somewhat close to DiCaprio. The other three guys here were just happy to be there, right? Redmayne and Cranston and Fassbender, they had zero shots. I would say Matt Damon had like 0.01%. Like if there had been someone in a film that was doing very well that award season, like even better let's say than The Revenant, then DiCaprio might have struggled a bit more. I think he still probably would have won, like no matter what actually. But it might have been a little bit more suspenseful, right? We might have gone into Oscars night, well it's probably going to DiCaprio. But what if they go all in on this other movie? Like this other film could win picture and director and maybe actor. If that had happened, we might not have been like 100% sure what the outcome was going to be. Because there just wasn't any competition really in best actor that year, DiCaprio skated to his Oscar victory. Reason number three is that The Revenant overperformed at both the box office and at the Oscars. That helped DiCaprio too. If it was just getting into best actor everywhere, like it wasn't getting into picture director, some of the reviews were just so-so, and people thought it was a good film, not a great one. And DiCaprio was just showing up from the globe to the Oscars in that category, but The Revenant was not being nominated anywhere else. You know, I think DiCaprio still probably would have won, kind of like how the year before Julianne Moore won for Still Alice at the Oscars, even though that film wasn't really showing up anywhere in any other category. She had an overdue narrative the year before for Still Alice. She still won, even though Still Alice is not in picture and director, supporting actress, screenplay, anything. DiCaprio still likely wins for The Revenant, even if that happens. But because The Revenant is in picture, it wins best director, it wins cinematography, people really love the movie, and it wasn't just like an awards film, you know, like an artistic achievement, it also was a box office smash. When it went wide in January, that film did huge numbers. I mean, I remember it got my grandfather Ralph into a theater to see The Revenant, and he never went to the movies. Like in my entire lifetime, he maybe saw three films in a theater, and he wanted to see The Revenant. So that film was appealing to a huge audience, like not just older people, younger people, it was for everybody. So the big box office numbers in January going into February, that sealed the deal, man. Like the fact that the movie was doing well with critics and with audiences, and doing really well in theaters all around the country, like that meant that DiCaprio was winning his Oscar. Reason number four was the narrative surrounding the difficulty in getting The Revenant made. Like all of those reports coming out of the production of how like things were getting shut down, how people were getting injured, how difficult every step of the way it was to make The Revenant, and how DiCaprio was really like suffering for his arts, right? I remember reading reports about that long before the movie came out, how hard it was for everybody involved, the actors, the director, the cinematographer, to get that movie to completion, and everything DiCaprio had to go through in that film. Just from a physical standpoint, like the scene with the bear, like what he has to do like on the set just for that scene, you know, and how physically he just he's aching that whole movie, right? He's walking, he's running, he's in pain and agony, he looks awful, you know, he's fighting, it's bloody, he's on the river, it's just it's like one thing after another. You watch the film, you appreciate his performance, but you also know he did go through hell making the actual film, so that was another reason why he won, which leads into the fifth and final reason, like the performance itself is very strong. This is not one of my favorite performances of the 2010s to win an Oscar. I still think his win should have been two years before for The Wolf of Wall Street, but I cannot come on here and say he's not doing very good work in The Revenants. It's often a remarkable performance emotionally and physically. What he is called upon to do throughout that narrative, it's, I mean, it's like guys, it makes sense why Leo won his Oscar for best actor. It's almost like after The Wolf of Wall Street, he met with his representatives, you know, he met with his crew and he said, I want to win an Academy Awards. What do I need to do that? Let's team up with Alejandro G. and Ari too, and cinematographer Emmanuel Lubezki, and let's go to hell and back making The Revenants. That is going to seal the deal for me, and it did, and no matter how obvious that victory was, like the foregone conclusion DiCaprio was finally winning his Oscar that night, it was still incredible, right? Triumphant to hear Julianne Moore call out his name, like finally he had won an Academy Award. There of course was a huge standing ovation for him, so well deserved. It was one of my favorite moments of the night to see DiCaprio holding that gold statue, about damn time. Let us not take this planet for granted. I do not take tonight for granted. Thank you so very much. So those are the main reasons why DiCaprio finally won his Oscar for The Revenants. It has now been a decade. As of this recording, he has received one more Oscar nomination for Once Upon a Time in Hollywood 2019. He was really good in Don't Look Up, he got into a couple places, did not get the Oscar nomination. He's of course very good in Killers of the Flower Moon, got into the Globes, did not get into the Oscars. So right now, we are all wondering, a second Oscar trophy in the years to come. Can he win again in Best Actor for One Battle After Another, directed by Paul Thomas Anderson, which is getting the best reviews of any film of 2025 right now. I think most of us have put DiCaprio back in at the Oscars in Best Actor. I had him out for a moment there, and he is back in. He's definitely getting nominated, it looks like, at the 98th Academy Awards. In exactly one decade since he won his first Oscar in Best Actor for The Revenants, can he win his second Oscar in the same category for One Battle After Another? Only time will tell. Thanks so much for watching and subscribing, and let me know in the comments below, what do you think of DiCaprio's Oscar victory for The Revenants, and I'll see you next time at the Awards Contender.