Why is Leo's project selection better than other A-listers'?

It's less to do with him being much more talented than his contemporaries and more because he is the last truly reliable box-office guarantee and because of that, he will always have first dibs on any project because all auteurs want their films to be commercially successful so that they can keep making their passion projects.

He grew up on 70s movies that everyone loves including Montgomery Clift films and always talks about how he is striving to reach that quality or come close to those classic films like A Place in the Sun or the De Niro/Scorsese collaborations. Stephen's point is also true. He is fortunate (and deservedly so) that he can shepherd projects like KOTFM and get people like Scorsese involved because he is a proven draw.

DiCaprio's a fascinating case because even though Titanic "made" him in terms of being a billion-dollar box-office grosser when that number actually meant something, his 2000s were somewhat rocky. He did The Beach immediately after and got largely excoriated for it, but it didn't have the cultural footprint to really ruin him. And DiCaprio actively tried to repudiate the pretty boy title by glomming onto Scorsese who, at the time, was starting to get that overdue narrative and making more awards-friendly projects. Gangs of New York and especially The Aviator were true tests but as you say, this was also the era of Depp's big comeback, Damon riding high off goodwill (hunting) and being a rival to DiCaprio's crown, and Clooney's zenith. But all of those guys were working far more frequently than DiCaprio, who was taking one or two years off between projects (even if he would have three years in that decade where he released more than one film). I've posited before that those double-headers helped his career more than if they had come out in consecutive years, as it helped make DiCaprio be seen more as an "event" actor that you had to wait for. And he pursued that much harder in the 2010s.

The Olivier argumet was he COULD do what James Mason did but Mason couldn't have done what Olivier did at the level he did it - he wasn't "the man"........that's arguable, but it isn't simple - it isn't Djokovic being the undisputed Tennis GOAT or another sporting metric like that. Saying Mason was a better actor than Olivier is what I say when I say Willem Dafoe is a better film actor than ANY 80s American (an overrated class imo) - that's very arguable but I could make such a case - not a bigger star, not the biggest box offce draw but a better actor........

There tends to be a few arguments for "the best" actors - who did it first? Who did the most total great work? Who at their best was THE best? Etc.

DDL almost by himself added another metric - the most consistent........does that make him "the best"?  Not to me  ........but if you thnk Henry James is "the best writer" because he didn't churn out crap for cash ..........well you could value that metric higher than I do myself.......that's fair.......

All three of the guys you mentioned are bankable mostly within their franchises (Bourne, Ocean's, Pirates of the Caribbean) and have spottier records outside of that - Depp significantly less so than the others in the 2000s.

Leo didn't do a franchise, kept himself sparse, and worked exclusively under respected auteurs (mostly Scorsese, the most respected American filmmaker). For audiences, he developed an association with unique, quality films and was rare enough for it to still be notable anytime he was out promoting projects. Everyone else ended up hitting slumps or having the loss of the home video market fuck their commercial prospects and the type of movies they could get off the ground.

Geez, seems like he starred in more than that.

Yeah, Damon is a workhorse. Probably part of the reason he's taken for granted. He's never not in something.

He also had a family to support. DiCaprio's famously not tied down and can afford to take whatever time away from filmmaking to live his life and do what he wants.

Oh for sure! Didn’t mean to discount that, but you hear sometimes about an actor/movie star hitting the big time and having all this financial/career success but in the back of their mind they are always that struggling actor wondering if they could make a living at this especially if it takes them “a while” to make it. I definitely see that with Samuel L. Jackson as Scrud said, Sam has enough generational wealth that he could’ve been retired, but he loves working and probably thinks back to when he didn’t make it until his mid-40s. Denzel is another one, etc.

I've had this discussion before, but I don't know why people talk about this as "choices" from Leo. Every actor out there would kill to play the lead in a Scorsese, Tarantino, or Nolan movie, it's not that nobody else wanted to do it and Leo "chose" it, he's just the first choice for everything. That's because he's the last actor left who can consistently open adult dramas and has done a good job schmoozing a list directors.

To address some of the other guys, Clooney was never even close to that level as a BO draw (where's Good God to go on his Clooney rant when you need him) and Depp and Damon did get plenty of good parts in the 2000's until they dropped off in the 10's. The "last movie star" narrative with Leo didn't really get going until his Wolf of Wall Street/Revenant era when he was getting those movies to grosses they clearly would not have gotten with any other actor.

You can't compare DiCaprio ( age 49) to Clooney ( age 62). Not the same generation, had different entry points to stardom ( DiCaprio became a star as a teen, whilst Clooney was a D-lister for over a decade before becominga TV star with ER and transitioning to movie stardom in his late 30's). And they weren't in competition for roles either

DiCaprio literally had the kind of head start into A-list stardom that very few actors get. It didn't really feel like he had to go through the same struggle many A-listers went through to reach the top.  We know who Leo's generation were, and none of them had the easy ride to stardom he did ( Damon, Bale, Phoenix, Norton etc), so of course their choices would be different. None of them were in the same position as him.

I don't agree.  They misused their privilege, at least compared to him.  There's no reason Norton after American History X couldn't dictate how his career would proceed.  It's so clear to me that DiCaprio just plain cares more than these guys, however comparable in pure acting talent they are.  Damon muddies things a bit, but Norton?  What a complete fucking underachiever if there ever was one.