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Ben Stiller, left, plays a 40-something documentary filmmaker struggling with his age in While We’re Young, a new film by writer and director Noah Baumbach.

Dan Hallman/The Associated Press

Don Draper is not alone. In the final episodes of the TV series Mad Men, the advertising exec played by Jon Hamm (who is 44) is struggling with many things, not least of which is his desire to stay relevant as his times are a-changing. Draper's self-worth is predicated on being the coolest cat in any room, but he's realizing he's become the square. Should he go gently, or rage on? I'm seeing that struggle everywhere these days.

In the new film While We're Young, now playing in select cities, a couple in their 40s (Ben Stiller and Naomi Watts) becomes enamoured with a couple 20 years younger (Adam Driver and Amanda Seyfried). Stiller's character – a tortured documentary filmmaker who admits that he's usually either "wistful or disdainful" – envies the confidence of the younger couple, and marvels that, unlike him, they're "doing their 20s right." He's torn between a desire to mentor Driver (who's also a documentary filmmaker) and the urge to crush him. He's eager to try new things – a hipster block party, an ayahuasca ceremony – yet embarrassed by being the oldest person there. The film's writer/director, Noah Baumbach, who is 45, told me in a phone interview that he feels his own youth was "both yesterday and eons ago."

In the upcoming drama Beyond the Reach, due April 17, Michael Douglas (who is 70) plays a sickeningly rich corporate raider who hires a guide (Jeremy Irvine, 25) to take him hunting in the Mojave Desert. (Irvine, who is English, also starred in Steven Spielberg's War Horse.) After an accident, Douglas's character ends up hunting Irvine's, and the generational conflict is as glaring as the desert sun: Douglas, an Earth-destroyer in a $500,000 custom-made SUV, who believes he's still a master of the universe, becomes increasingly incensed that Irvine, an ecoconscious pauper with washboard abs, can both outrun and outwit him.

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In another upcoming drama, The Forger, due April 24, John Travolta, 61, tries to bond with his son (Tye Sheridan, 18, who co-starred with Matthew McConaughey in Mud and Brad Pitt in Tree of Life) by pulling off one last big job. Further complicating matters: In both While We're Young and The Forger, the protagonists are squeezed not only by the younger generation that's replacing them, but also by an older generation who mocks their panic. Charles Grodin, 79, playing Stiller's more successful father-in-law, is scornful; Christopher Plummer, 85, playing Travolta's father, cracks wise.

This question is everywhere now, I think, because the people who remain in charge of mainstream entertainment have the perception that being 70, or 61 or even 44 is not what it used to be – that diet and exercise, staying connected electronically and keeping up with trends, has enabled people to stay "younger" much longer. The characters played by Stiller, Douglas, Travolta and Hamm still believe they're feisty game-changers who bestride the world like colossuses – until they're confronted with someone who is truly, biologically young. They're mortified to realize that in the eyes of twentysomethings, their ways of thinking and behaving are outdated – at best, they're somewhat amusing; at worst, simply old. When I was growing up in the 1970s, the generational rallying cry was, "Don't trust anyone over 30." For millennials, it's more like, "Pat anyone over 30 on the head condescendingly." That stings.

Baumbach has heard opposing reactions to While We're Young. "Some people say, 'You clearly hate hipsters,'" he said. "Others say, 'It's great how even-handed you are.'" He deliberately cast his film in a tried-and-true genre, the comedy of remarriage, which ranges from Shakespeare's Much Ado About Nothing to Cary Grant screwball comedies such as The Awful Truth. In his creative life, Baumbach feels "productive and relatively good," he said. "And there are good things about being older. You know yourself a bit better. You can be in your life more easily. There's some relief in giving up on trying every new thing."

But he also confesses that if he's listening to the radio, he'll opt for "whatever station is most likely to play Don Henley's The Boys of Summer," and that he's "sitting out" social media. And though he jokes about it, he's felt the shudder of mortality. In While We're Young, when a doctor diagnoses Stiller's character with arthritis, he can't process it. "Arthritis arthritis?" he asks. "Well, I usually just say it once," the doctor deadpans.

"That, to me, is the worst thing about middle age," Baumbach said. "When you were younger and went to a doctor, he'd laugh off any complaint. Then you reach an age where you tell a doctor the same complaint and he says, 'Let's get you an MRI.'" He laughed. "It's so human, thinking that we're not there yet. But we're always there."

Douglas, who's been working steadily since 1969, when he was nominated for a Golden Globe for "new star of the year " (he lost to Jon Voight), has the relaxed power that a lifetime at the apex of showbiz brings. Last September, when Beyond the Reach premiered at the Toronto International Film Festival, he clearly commanded any room he was in. He knows his film is timely, he told me: "Every movie I've done is contemporary. I read newspapers. I like current events."

But of course, that newspaper reference plants Douglas firmly in the 20th century. And he's no stranger to how the reins are passed from one generation to the next – he took over from his own father, Kirk. So he's all business about his place in the Hollywood firmament. "I like that I'm working," he said. "I'm happy I get parts. This one is a gamble. Independent, low-budget. I saw it as a chance to attract a younger audience."

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Travolta, with whom I also spoke at TIFF, was as famous as anyone has been – when his breakout TV series, Welcome Back, Kotter, was airing, 40 million people routinely tuned in. He sees his career as a mosaic: the early days, when his films Saturday Night Fever and Urban Cowboy defined the zeitgeist; his middle years, kick-started by Pulp Fiction, when Primary Colors landed him on the cover of Time magazine; and now. Though he can still knock the young'uns off a screen, as he did with Taylor Kitsch and Aaron Taylor-Johnson in Oliver Stone's Savages, "I'm in the last era of my life," Travolta admitted.

"I can see it winding down," he continued. "But I want something to do. I don't want to retire. I want to be Christopher Plummer. That means I have 25 more years. The trick is to stay in good health and have your wits about you."

At the end of his latest novel, Funny Girl, Nick Hornby (who's 57) poses this same question: Should older people accept that their time has passed, make a dignified exit and finish their days pottering in their gardens; or should they fight to stay in the game until the end, risking humiliation and marginalization in the process? Hornby's answer, like Baumbach's, Douglas's and Travolta's, is clear: "I'm 'work till the end,'" he told me recently.

On the other hand, Don Draper – who, as a fictional character, is permitted fewer self-delusions – may present a darker answer. We'll see in a few weeks where he lands.

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