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Alec Baldwin Is Having the Last Laugh

The latest installment of Misleading Men, the series where we look back at actors who ruled Hollywood for one brief shining moment

Some actors are as famous for the roles they lost as the ones they landed. Eric Stoltz was initially cast as Marty McFly in Back to the Future, only to be replaced a couple weeks into production when the filmmakers decided he wasn’t right for the part, paving the way for Michael J. Fox’s big-screen stardom. Tom Selleck was set to play Indiana Jones in Raiders of the Lost Ark, but he couldn’t get out of his Magnum P.I. contract, so Harrison Ford donned the fedora.

For many years, it seemed like Alec Baldwin’s career was going to be another example of this odd phenomenon. A respected actor, a recognizable name, and yet, according to conventional wisdom, he shot himself in the foot when he lost Jack Ryan, the character that helped make him bankable thanks to the 1990 blockbuster The Hunt for Red October.

Happily, though, Baldwin hung around long enough to rewrite that narrative. In fact, 27 years later, he’s once again the lead in a major studio movie with the animated family film The Boss Baby — and although it’s a very different type of role, in a weird way, it’s an extension of everything he’s done since Red October.

Baldwin, who turns 59 on Monday, grew up on Long Island with three brothers who all went into acting (Billy, Daniel and Stephen), two sisters and his parents, who were both teachers. “I think I’m just like a lot of people who had nothing,” Baldwin told Vanity Fair in 2012. “We had to amuse ourselves, so we had to become amusing. My brothers were funny, and there was a lot of shtick and comedy and nastiness and violence and fighting and sports.”

Baldwin’s father wanted him to become a lawyer. And when Baldwin attended George Washington University in the mid-1970s, he had his eye on law — with a run for public office, even president, in the back of his mind. “I wanted to be president of the United States. I really did,” Baldwin told Interview magazine in 1989. “The older I get, the less preposterous the idea seems.”

But as a 2008 New Yorker profile explained, Baldwin changed course after breaking up with his girlfriend in his junior year and losing a student-body election. Instead, he jumped ship, entering NYU’s Tisch School of the Arts to pursue acting. “Without a doubt the most looming memory I have of NYU was simply being in New York. That was always the fantasy,” he recalled in 2010. “I wish I had gone to NYU the whole time. I mean, I liked GW, I wouldn’t put it down, but I loved NYU. Living in New York was just — I got high every day just doing that.”

Baldwin has always possessed the wary, tough-guy energy of a true New Yorker, and after Tisch, he stayed in the city, landing a role on the soap The Doctors in the early 1980s. After a stint in L.A. to work on Knots Landing, he returned to the Big Apple for a revival of Loot, his Broadway debut. “My whole introduction to this business was: If you don’t do something in the theater regularly, you’re nothing, you’re a shit,” Baldwin told Interview. “The minute I get the chance, I go back and do that, because it really does help you. Psychologically.”

Still, the allure of working in film was too much, and soon his career took off. His first major part was in 1988’s She’s Having a Baby as the best friend of Kevin Bacon’s married man. Baldwin’s character just so happens to have feelings for his Bacon’s wife, played by Elizabeth McGovern. (Funny enough, Baldwin had replaced Bacon in Loot when it made the leap to Broadway a couple years earlier.)

She’s Having a Baby demonstrated the actor’s tempestuous soulfulness, and it was just the start of a good year for Baldwin, who had five movies out within the span of 10 months, including Beetlejuice, Married to the Mob, Talk Radio and Working Girl. He really popped on screen, but in each, he was always the supporting character. As he told Interview about working on Talk Radio, “[Director Oliver] Stone is impenetrable. I don’t even bother to try to figure him out. And that’s not a judgment of him. Eric Bogosian was the lead in the movie, and the special relationship that the lead had with the director is reserved for the lead only. One of the reasons Red October was such a rewarding experience was that I was the lead in the movie.”

Based on the Tom Clancy bestseller about a rogue Soviet submarine commander (Sean Connery) and the CIA analyst (Baldwin) who’s trying to figure out where he’s headed, The Hunt for Red October opened in March 1990. Connery was the big star, but Baldwin was the film’s center as Jack Ryan, a likable underdog who’s constantly convincing his superiors he knows what he’s doing. Baldwin is fabulous in the role — funny, smart, empathetic — and the film was a critical and commercial success, ending up as the year’s sixth-highest-grossing movie.

Roger Ebert zeroed in on what made Baldwin so engaging as Ryan, writing that the actor “has the looks of a leading man, but he dials down his personality. He presents himself as a deck-bound bureaucrat who can’t believe he has actually gotten himself into this field exercise.”

After The Hunt for Red October, Baldwin seemed set for superstardom. But that didn’t happen. Instead, he quickly became known as the guy who blew his chance to do more Jack Ryan movies. Harrison Ford stepped into the role for Patriot Games and Clear and Present Danger, the latter of which became the most commercially successful entry in the Tom Clancy franchise. For his part, Baldwin claimed that he had to pass on Patriot Games because he was already committed to starring in A Streetcar Named Desire on Broadway. However, Baldwin’s brother Billy told The New Yorker’s Ian Parker that “to a certain extent, [Alec] played chicken” when negotiating to do Patriot Games, which ended up biting him in the ass. Regardless, Baldwin spent the rest of the 1990s mostly making crap. He did a big-screen version of The Shadow. He starred in an adaptation of Jim Thompson’s novel The Getaway with his then-wife Kim Basinger. He made dull thrillers like Malice, Heaven’s Prisoners and The Juror.

Recalling this fallow period, Baldwin told Parker in 2008, “I ignored all of my instincts and started to do what other people suggested I do, but I knew it was wrong.”

With each subsequent bomb, the legend of Baldwin’s failure to hold onto the Jack Ryan series grew larger, threatening to make him one of those actors who’s remembered for whiffing at his chance at greatness. And although Baldwin was part of movies like Pearl Harbor, State and Main, The Aviator and The Departed — and was nominated for a Best Supporting Actor Oscar for 2003’s The Cooler — his golden opportunity seemed to have slipped away. “Do you want to know the truth?” Baldwin confided to Parker. “I don’t think I really have a talent for movie acting. I’m not bad at it, but I don’t think I really have a talent for it.”

It was then he was saved by television — although, really, the seeds of his renaissance had been sown years ago, in the strangest of ways. In the midst of his Red October breakthrough, Baldwin did two crucial things. The first is that he hosted Saturday Night Live for the first time, on April 21, 1990. The second is that he landed a small part in the big-screen adaptation of Glengarry Glen Ross, the Pulitzer Prize-winning play from David Mamet, who was friends with Baldwin.

Mamet essentially kept his original play intact, but for the film, he decided to add a scene where the browbeaten real-estate salesmen (played by Ed Harris, Alan Arkin and Jack Lemmon) are admonished to boost their sales or get fired. Baldwin desperately wanted to be in the film and cajoled Mamet into writing this part for him for the most manipulative of reasons — at dinner one night years earlier, the playwright had forgotten his wallet, and Baldwin paid the bill, a debt he later exchanged for the role.

And so, the world saw Baldwin as Blake, who’s come to deliver the emasculating pep talk that sets the film in motion. It’s one of the decade’s most famous and quotable monologues:

Outside of The Hunt for Red October, those seven minutes from Glengarry Glen Ross are the best thing Baldwin has ever done on the big screen. And soon, Baldwin’s speech started to soak into the culture. You saw echoes of it everywhere. 2000’s Boiler Room featured Ben Affleck performing a riff on it. Five years later, Baldwin did a Santa’s-workshop parody of it in a skit called “Glengarry Glen-Christmas,” in which he comes to browbeat the elves into working harder to get all their toys made before Christmas Eve. In fact, there have been so many references to Baldwin’s machismo-overdrive “Always Be Closing” speech throughout the years that The Atlantic was able to do a whole roundup of the best homages for the film’s 20th anniversary.

All the while, Baldwin was making frequent stops on Saturday Night Live, becoming one of the show’s most reliable hosts. (He is also the program’s most frequent host of all time, with 17 appearances.) His film career may have been waxing and waning, but SNL helped give him an outlet to show off his understated comedic talents. They were not lost on head writer Tina Fey, who thought he’d be perfect to play the boss on a sitcom she was developing.

30 Rock is ostensibly about Fey’s Liz Lemon, the overworked showrunner of an SNL-like sketch program. But it was Baldwin’s Jack Donaghy who was the sitcom’s breakout character: a numbers-obsessed NBC executive who becomes Liz’s reluctant mentor. What made Jack hilarious, of course, was that he didn’t know how funny he was — a trait he shared with the guy who played him. In the midst of 30 Rock’s run, Baldwin appeared on Comedians in Cars Getting Coffee and told Jerry Seinfeld, “I don’t think I’m that funny. I learned a lot from being around them for six years — they taught me a lot.”

Nevertheless, he won two Emmys for the role, which mocked not only corporate suits but also the younger Baldwin. During one episode, when Jack walks in front of a high-tech HD camera, which amplifies the person’s physical features, the image we see on the monitor is that of the impossibly handsome and noticeably thinner Baldwin from The Hunt for Red October.

Baldwin’s newfound funny side has continued to reap huge benefits. This season on SNL, he has appeared frequently to play Donald Trump, a performance that helped propel the show to excellent ratings. In a sense, his Trump was merely a crueler, dumber version of Jack Donaghy: pure greed and self-regard without the leavening humanity. And now this Friday comes The Boss Baby, which basically looks like the animated kids’-movie version of Jack Donaghy — complete with yet another parody of “Always Be Closing”:

Baldwin’s outspoken, unfiltered New York energy gives his characters their edge and their compelling authenticity. But that intensity has too often bled over into his real life, resulting in ugly incidents — the threatening voicemail he left his 11-year-old daughter in a blind rage; his high-profile divorce from Basinger; the gay slur he hurled at a photographer in 2016. With that history, it’s remarkable that anybody would decide he’d be the perfect choice to voice an adorable toddler for a big-budget family film. That Baldwin remains largely in the public’s good graces may come down to the fact that some of his most iconic roles have conditioned us to expect him to be, well, an asshole.

Starting out, Baldwin could have hardly anticipated how his career would evolve — from rising blockbuster star to commercial dud to respected character actor to unlikely TV sitcom sensation to The Boss Baby. In that 1989 Interview profile, right before The Hunt for Red October came out, he proclaimed, “I don’t think I’m going to do this for the rest of my life — become a movie star, make millions of dollars, and just do that, travel and go to Cannes, have my picture taken and all that bullshit.” At the time, he was alluding to an eventual run for political office. But it turns out his prediction was right — just not in the way he imagined.