When people reminisce about the career of beloved comic Robin Williams, you rarely hear talk about his 2006 political satire Man of the Year. There’s a reason for that.

Williams plays Tom Dobbs, a late-night, fake-news comic who is so popular that he jokingly runs for president. (It wouldn’t have been hard to imagine Jon Stewart getting plenty of votes in 2006.) But what could have been truth-to-power comedy turns into a stream of obvious half-jokes, delivered by a strangely subdued Williams. The Orlando Sentinel called it “a nearly tone-deaf satire of American politics and the culture of celebrity, a comedy without enough laughs, a satire without enough bite.” The A.V. Club agreed, saying Man of the Year “ends up feeling as phony as the process it so desperately wants to skewer.”

If there’s anything prescient about this movie, it’s the idea of an entertainer running for president who’s more surprised than anyone when he wins.

Let’s talk about Don’t Drink the Water partly as a reminder of how much people can change over the course of 30 years. Try telling 1994 Michael J. Fox and Woody Allen what their lives would look like in 2023. The fact that Blossom is hosting Jeopardy is the least of it.

Allen’s clunker involves a vacationing family in Eastern Europe who wanders off the beaten path and sees things that a family shouldn’t see behind the Iron Curtain. Allen, wife Julie (Marge Simpson) Kavner and daughter Mayim (Blossom) Bialik are forced to take refuge in an American embassy, run by the bumbling Fox. Just for fun, Dom DeLuise wanders in from a Burt Reynolds movie doing magic tricks and setting things on fire.

Despite its setup as a satire about East/West relations, Don’t Drink the Water has little to say about how the world works. It’s way more interested in a tepid romance between Bialik and Fox than in ambassadors and diplomacy. Allen stammers and bumbles his way through the mess, a remake of a 1969 version starring Jackie Gleason that was even worse.

Just call this “John Travolta is Bill Clinton!” because that’s exactly what Primary Colors is. Amazingly, it was released in 1998 while Clinton was still in office. Too soon? Maybe, at least in terms of getting enough distance to even know what it was trying to satirize.

In the moment, Primary Colors actually got good reviews for Travolta, as well as Emma Thompson starring as, well, Hillary. Director Mike Nichols was once again collaborating with old writing partner Elaine May, so you can count on them for laughs if nothing else. But as satire, it was largely toothless. Clinton, er, Jack Stanton likes to eat fast food? He flirts with pretty gals? That’s all funny-ish fodder for a Saturday Night Live cold open, but it doesn’t tell us much about the state of late 20th-century American politics. 

One rationale for casting a dazzling array of stars (Leonardo DiCaprio, Jennifer Lawrence, Ariana Grande, Jonah Hill and Meryl Streep — say what now?) is that we’re so busy recognizing famous faces that we might ignore a half-baked message. But even with an all-star cast, Don’t Look Up still can’t deliver on its aspirations, be they satirical, political or apocalyptic.

In Don’t Look Up, two scientists discover that a meteor is about to destroy the world, but they’re unable to get anyone to take the threat seriously. It’s just like climate change, get it? Or maybe it’s just like the COVID-19 vaccine? At any rate, people just won’t listen!

Don’t Look Up has plenty of anger directed at… us, we guess, the dumb sheep who turn a blind eye to global problems, too distracted by Instagram and Netflix to care. But director Adam McKay doesn’t know what he wants the great unwashed to do exactly. There’s plenty of bluster and outrage here — one can practically taste the condescension McKay feels toward his audience. But Don’t Look Up flounders when it gets to the part about what McKay expects anyone to do about a seemingly unstoppable catastrophe. Maybe he believed that all those stars would at least make us look at our impending doom. 

If it’s laughs you’re after, you won’t find a better bet on this list than 1998’s Bulworth. Unfortunately for the film’s creators, we’re laughing for all the wrong reasons.

Blame Warren Beatty for all of it. He’s the guy who starred, directed and co-wrote this political satire about a disillusioned senator ready to end it all before he hooks up with a young, Black political activist (Halle Berry) who teaches him how to rap? Spending time with her poor family in South Central makes the proverbial light bulb go off over his head, eventually telling a television audience that “everybody should fuck everybody” until we’re all the same color. Much of this is rapped, by the way. 

Please, make it stop. 

Amazingly, many critics bought this crap in the moment. Time Out called it “a sharp, brave movie.” The New York Times said Bulworth “works, with both urbanity and chutzpah.” The San Francisco Chronicle applauded, writing, “Beatty has fashioned a hilarious morality tale that delivers a surprisingly potent, angry message beneath the laughs.”

But time has not been kind to Bulworth. If the idea of Beatty rapping appeared edgy and brave in 1998, it smacks of cringe and cultural appropriation now. Even in the moment, there were plenty of arched eyebrows when Berry’s character tells Bulworth, “You’re my (n-slur).” A more contemporary reading of the movie by Splice Today calls Bulworth “racist bullshit,” condemning the movie’s argument that “there are no Black leaders because not enough white senators are into hip-hop.” 

The white savior trope is a clumsy one, and rarely more awkward and sad than in Bulworth.