Is Brad Pitt this generation’s Robert Redford?

It’s a Natural comparison.

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Is Brad Pitt this generation’s Robert Redford?

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Which "generation" would that be, exactly? Dude's a Baby Boomer.

I don’t see why not. Many mutual traits, most notably the ability to mix vulnerability and strength in the same moment.

i'm glad brad pitt has been getting his flowers lately. he's the man (no homo).

The reason why Pitt didn't start to get accolades until late is that Hollywood was blinded by his aesthetics and wanted him to be the pretty boy leading man right away and in parts for which he not suited (e.g. Interview With the Vampire). Pitt wasn't going to be a "plug and play" leading man, just because he was handsome.

I could see it and dismissed him (as I must admit, I did with Leo, at least very early, because they pushed him so hard for every role) as vapid and talentless. However, over time, I really appreciated the quality work he did in support.

And there are a handful of times where he was in the lead and did really well (I would say Benjamin Button and Moneyball are my favorites with Pitt in the lead). But that key support role is where he really shined - Fight Club, OUATIH, and even the quirky smaller roles, Floyd in True Romance or Chad in Burn After Reading. He also did well in ensemble casts.

(ETA: No homo - NTTAWWT)

I like Spy Game with Pitt and Redford.

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I like Spy Game with Pitt and Redford.

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Tony Scott GOAT

There’s no doubt Brad Pitt filled a similar role to Redford both are good looking popular leading man types. But Pitt is a better actor imo. He’s a great character actor in a leading man’s body.

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He's really a tweener who is more Gen X than Boomer.

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Probably fair - a lot of the late boomers fall into this category. Even some guys who are more middling boomers (Alan Ruck and Judd Nelson are 2 that come to mind) fall into this "in between" or hybrid category, because of their relatively late rise to fame and their playing Gen-X characters up to a decade younger than their biological age.

Certainly Cruise ('62) and Pitt ('63, and December at that) are extremely cuspy. The easy definition of "the Boom" would run 1/1/46 through 12/31/63 - a period of 18 years. Event-driven folks might shift it, slightly, to mark the end of the Boom as being the assassination of JFK and that is subtle enough/close enough to move Pitt across the line to Gen-X. Pretty much the entire Brat Pack consists of late Boomers/early Gen-Xers. The "Brat Pack" extended family might include Cruise and Pitt in some folks' minds. Emelio, McCarthy, Demi and Sheedy would all fit your same qualification of "tweener, more Gen X than Boomer", all being born in 1962, same as Cruise.