This week HitFix is revisiting some of the key turning points in recent entertainment history and considering what would have happened if history had turned a bit differently. What if...?

There's a question I've turned over in my head a thousand times, and while there are music fans who I'm sure have very strong feelings about the tragic deaths of artists whose work was cut short, as a film fan and as someone who got hooked on movies in the '70s, who came of age in the '80s, and who moved to Hollywood just as the '90s kicked off, there is one question that looms largest for me, one that I feel strongly about as my first pick. If we're trying to imagine a world we wish had happened, this is question number one for me…

What if River Phoenix had lived?

WHEN WAS IT?

The night of October 31, 1993 still seems unreal to me, especially the way the news spread that River Phoenix had collapsed on the sidewalk outside the Viper Room. Living in LA, that conjured such a specific image, and it seemed offensive to think of someone as gifted as Phoenix suddenly simply not being there anymore. As a fan of his work, I was excited by each new film, knowing full well that we were still just seeing the start of what he could do. He managed to be casually great in a series of films, and I felt like we were seeing the warm-up to a huge adult career. And then... suddenly... gone.

WHO WAS INVOLVED?

River Phoenix, of course. Johnny Depp, whose Viper Room got an unwanted and immediate starring role in the death of this well-loved young emerging icon. Flea, who was the reason Phoenix went to the Viper Room that night in the first place. Rain. Joaquin. Samantha Mathis. The Film Industry.

WHAT WAS THE RESULT?

A huge seismic loss to film, of course, but also a direct hit to the personal lives of a number of talented people. I still can't imagine the pain of losing a brother under any circumstances, much less right there on the sidewalk, in plain view of the world, at the worst possible moment. The industry itself seemed to have to suddenly adjust because it was so obvious he was being groomed for major stardom. Without him, they had to create another new leading man, critically well-liked but also total crush bait.

Leonardo Di Caprio seems to have managed to build the sort of career Phoenix was well on his way to enjoying, and even with some great young talent working now, I can't help but feel like the whole business never quite recovered from what a miserable shot to the heart it was to hear this news in the first place, and I cannot imagine the ongoing pain of absence for his family, both parents and siblings, as they reach milestones or form memories that they wish they could share with him.

Here's the thing... until we talked about doing this "What If?" week, I had never really seriously contemplated the question, but when I realized it has been 20 years since he died, that seems like enough time to look at the business, the cast of characters in modern movies, his family as we see them today, Enough time has gone by that I am genuinely curious now.

Three things that wouldn't have happened:

1 - Shia LaBeouf never gets within a million miles of Indiana Jones

Let's be honest. One of the reasons people love "Indiana Jones and the Last Crusade" is because it has a stupendous opening sequence. River Phoenix had spent enough time with Harrison Ford on "The Mosquito Coast," and he was a clever enough mimic, that he gets every single physical twitch right in his turn as young Indiana Jones. It's an amazing opening, and if Phoenix lived, either he would have gotten his own spin-off series of films that would have replaced the creation of the TV version of "The Young Indiana Jones Chronicles," or the fourth film would have happened sooner, and had another flashback at the beginning, a good solid 20 minutes that would then give way to the real adventure.

Either way, there's no chance they ever introduce Mutt Williams. Who knows what the series would have looked like by the 21st Century with Phoenix alive?

2 - Leonardo Di Caprio might not have hit that iceberg

River Phoenix was well on his way to being a bankable star when he passed away. Acclaim was something that had become a given, and he was certainly not above making a decision that was about getting better opportunities and being able to help get something good made. He would have, at the very least, been in the running for "Titanic," and I can imagine Cameron wanting that perfect blend of credibility and commercial appeal, and someone a little older. After all, Phoenix was set to star in "The Basketball Diaries" at one point, and "Total Eclipse" is another role that was his at first. It is not a stretch to say that DiCaprio's early days could have easily been delayed or deferred if Phoenix was around to take roles away from him.

3 - Joaquin Phoenix would not have gone all "I'm Still Here"

One of the saddest parts of River's early death is that we never got to see him co-star with Joaquin, who was still "Leaf" back at that point. Joaquin's early work in films like "Parenthood" certainly made him seem like he had a much more bruised and vulnerable persona than River, but with his older brother around to bounce off of, there's a good chance Joaquin would have been a different person, less haunted. I still don't think "I'm Still Here" is pure performance art just for the sake of it. Looking at the best work Joaquin does on film, it all leans on that pain that seems such a real part of his persona. With River around as a support system, I wonder if we would have seen such a troubled young man, or if maybe we'd see a lighter version of the actor he's become.

Three things we predict would have happened:

1 - He would have branched out from playing sensitive young men

Phoenix perfectly embodied an archetype of the sensitive young man who is trying to chart an emotional course through a painful world, a niche that guys like Johnny Depp and Leonardo Di Caprio were only too happy to fill in the wake of Phoenix's death, and one that Ryan Gosling is getting maximum mileage out of today. The thing is, you can only do that for a certain amount of time without either tipping into self-parody or just plain going insane. Phoenix was underappreciated as a comic presence, and I believe that would have changed if he'd been around for even five more years. His comic timing was amazing, and because he never played a scene as a "joke," he made even his most absurd moments feel real. We never got a sense of his full range as an artist, and it would have taken time for that to finally happen.

2 - He would have sold a whoooooole bunch of records

Music was a significant part of Phoenix's creative life, and when he made "The Thing Called Love" for Peter Bogdanovich, he ended up writing and performing a lot of his own music in the film. It was part of his life from when he was very young, and he was in a band with his sister Rain called Alekas Attic. I don't know if he would have kept that band or some version of it active, but music would have remained an important part of who he was, and if "The Thing Called Love" is any indication, he had genuine chops as a songwriter. It's not always pretty when actors release albums, but Phoenix seemed like the kind of guy who could easily have made it work, especially considering what a passionate fanbase he already had.

3 - He would have had a whooooooole bunch of Oscars

That Oscar nomination in 1989 was just the warm-up. Phoenix was beloved by the filmmakers he worked for, the actors he worked with, and the general public. He wasn't someone who seemed excited about the publicity game, but he also wasn't so afraid of it that he constantly self-sabotaged the way some actors do. He was political enough that he could have played the game without giving up any of his integrity, and because he worked for filmmakers like Sidney Lumet and Steven Spielberg and Peter Bogdanovich, he would have had support across several generations of Hollywood talent. There is no way he would have kept working and gone unrewarded. It was just a matter of landing the right role in the right year, and considering how he was the top of everyone's list on almost any project he was even remotely right for, I'm guessing he would have had many opportunities to take home Hollywood's best-known award.

Did history work out for the best?

Nope. We lost something special when we lost Phoenix. Oddly, I don't think it's the 20 years since his death that are the most painful, but the years that would be ahead now for the 40-something year old star. Watching him become a man, seeing how he followed his tastes and his interests, was something that I think most of his fans were looking forward to, and I still wonder sometimes when I see a film he could have starred in how it would have been different with him playing the part. There are lots of talented and eclectic actors working today, but no one who offers up that same combination of talent and charm and charisma that Phoenix had. I don't consider every death tragic automatically, but considering it's been two decades and this one still hurts like it's fresh, I think this stands as one of the greatest sorrows I've seen this industry sustain in the time I've lived and worked in LA.

During Comic-Con, I got a chance to chat with Lili Taylor a bit, and she was exactly as lovely and warm and funny as you'd hope. When we started discussing "Dogfight," which may be my favorite Phoenix film, the reaction she had was immediate and almost overwhelming. I saw tears in her eyes as we talked about Phoenix and about the experience of making that film with him for director Nancy Savoca. There's a remarkable moment in that movie, a pivot point for his character, where he is watching her sing and play the piano, and for him, it's a silent scene, a slow push-in as he realizes who this person is. When I think of that moment, it sums up everything that was wonderful about him. It is a moment of intense, wide-open humanity, a person laying bare the things we all struggle to keep covered up every day, and that gift of his obviously left its mark on the people he worked with and the people who watched that work.

What if? Man, I wish we knew that answer.

I'll have a few more contributions to "What If?" week as it continues, and keep checking in all across HitFix for special contributions from our music and TV writers also examining possible alternate realities.