Is Will Smith the last 1990's Movie Star to Win His First Oscar?

There are so many sites on the internet that talk about the immediate Oscar race that I generally steer clear of it outside a few key articles every season, but that doesn't mean I don't think about the Oscar race constantly.  I have avoided talking about the biggest controversy right now (the heinous, unforgivable sin of moving a bunch of the categories off of the main broadcast to allow for a Twitter poll that's going to, I don't know, make people see the clip of The Matrix slow motion for the 1000th time?), mostly because I'm on record as saying this is a terrible idea (the way to "fix" the Oscars is to lean into the traditions, not exorcise them).  But I have realized recently that a strange phenomenon that has been happening intermittently over the past twenty years may well be coming to an end this season, and so I couldn't let this observation go by without commentary.

Barring something truly insane, Will Smith is going to win his first Oscar on March 27th for his work in King Richard.  I remember basically saying this was a done deal after seeing the movie, and despite some protestations that Benedict Cumberbatch or Andrew Garfield might sneak into the upset position, there is virtually no evidence that Smith is going to lose.  It's exactly the kind of role that Oscar loves-a biopic Best Picture nominee from a movie star actor who is doing his level-best to infuse some drama without losing any of his natural charisma as a performer.  Is Smith the best nominee of this bunch?  No, he is not. Is it possible that this win will age poorly, in a similar vein to, say, Gary Oldman's victory for Darkest Hour?  Possibly, especially if Andrew Garfield & Benedict Cumberbatch continue to go Oscar-less.  But this is a done deal-Smith has won every precursor for a reason, and is going to win this trophy.

Part of that is because the Academy loves giving trophies to movie stars.  Despite some people's complaints that the Oscars are an elitist organization, that doesn't really track.  Most Oscar winners are not Glenda Jackson or Peggy Ashcroft...they're John Wayne & Gregory Peck & Joan Crawford & Paul Newman.  They're big-name, marquee-headlining performers who have made everyone in that room rich and everyone at home shell out for tickets.  Smith is not unusual in this regard.

What is unusual about Smith is that he comes from a different generation of movie stars, some might argue the "last" generation of movie stars.  While we still have headliners in movies today, and so I don't love when people say "there are no movie stars anymore," it's fair to say that the last time that movie stars reigned supreme in a significant way in Hollywood, where a name launched a film's box office more than franchise, was the 1990's, which is when Smith hit his peak (albeit in the late 1990's).  Oscar has been milking the nostalgia for that decade, the last decade where movie stars (and not franchises or IP) ruled Hollywood, for over twenty years.

It's to be expected during the actual 1990's movie stars of that era would win, and indeed you see people like Tom Hanks & Gwyneth Paltrow armed with statues.  But it was in the decades that followed, where true Grade-A movie stars largely disappeared, that it became apparent that Oscar couldn't let go.  Since the end of the 1990's, by my count at least a dozen big-name stars of that era have won their first Academy Award.  You can quibble if one or two of these names don't deserve to be on here (or if I'm missing 1-2) but Julia Roberts, Halle Berry, Nicole Kidman, Kate Winslet, Sandra Bullock, Russell Crowe, Sean Penn, Morgan Freeman, George Clooney, Matthew McConaughey, Leonardo DiCaprio, & Brad Pitt all got their start in the 1990's as splashy, People Magazine-style stars, and in most cases reached their peaks.  Will Smith qualifies for this list, and continues that trend.

The question I have here, though, is if this is the end of such a trend.  Smith is not someone who, even a year or two ago, seemed inevitable to win an Oscar, certainly not in the way that DiCaprio or Pitt or Winslet did.  So it's possible we're underestimating a star of the 1990's.  Certainly there are still stars that work regularly from this era that could sneak in.  Tom Cruise is the name that comes most readily to mind.  Though Cruise was also a big star in the 1980's, his star shone the brightest in the 1990's, which was also when he seemed to genuinely want an Oscar (he scored three nominations in a ten-year span).

But Cruise doesn't make the kinds of movies that Oscar loves anymore, and hasn't really "acted" in at least a decade.  The rest of the 1990's stars of any caliber don't seem to factor.  Jim Carrey, Hugh Grant, & Adam Sandler are all people who might've gotten an Oscar nomination at some point, but don't really make the kinds of movies that Oscar notices, frequently leaning into paychecks more than stretching their talents.  Johnny Depp was definitely going to win an Oscar at some point, but that seems next-to-impossible at this juncture given the state of his public reputation.  A lot of stars from that era work infrequently (Demi Moore, Meg Ryan) or appear in film projects that aren't seen in the light of Oscar (Bruce Willis, Sharon Stone, John Travolta).  Some have shifted their focus to television (Winona Ryder, Uma Thurman, Drew Barrymore) while others weren't stars whose acting was taken all-that-seriously to begin with (Arnold Schwarzenegger, Keanu Reeves).  A few actors of note from the 1990's could get an Oscar (I'm thinking specifically of Annette Bening), but were really more "serious actors" more than they were ever thought of as more traditional "open a picture" movie stars.  And then there are a few actors who might still win Oscars, but whose stardom really belongs more to a previous decade (Harrison Ford, Glenn Close).

So I'm going to be honest here-the answer of if Will Smith is the final 1990's movie star to win his first Oscar probably lies with the last person who I think is a serious, true bet to someday win their first Oscar: Michelle Pfeiffer.  Pfeiffer was a three-time Oscar nominee, and you could quibble to a slight degree over whether her stardom belongs more to the 1980's or not, but I'd argue most of her commercial work as a movie star happened in the 1990's, so she qualifies.  Pfeiffer is a good actress, someone who still clearly has the goods to get a nomination.  She works infrequently, but not so much anymore that the right project couldn't come along in the same matter as Smith (she's not Meg Ryan, basically hibernating off-screen at this point).  As she gets older, it's not entirely clear if Pfeiffer, always apprehensive about celebrity, even cares if she's going to win or not.  But if there's still one more 1990's movie star left who could pull it off, she's the glaring example of someone who probably should have an Oscar by now but doesn't.  Without her, I have to wonder if Smith might truly be the last great 1990's star to get to hold a golden statue for the first time.