It’s been 25 years since the birth of the modern romantic comedy. Beginning with When Harry Met Sally… in 1989, the genre has become a launching pad for some actors and a refuge for others. In these movies we find predictable moments, heightened notions of love, and a lot of questionable outfits. And while the genre has morphed over the years, we’re still in love with rom-coms — so we’re celebrating them all week. Welcome to Rom-Com Week.

There is an alternate universe in which Paul Rudd becomes our next-wave Tom Hanks. He had the tools: the puppy dog charm; the unthreatening good looks; a deep well of finely cultivated, but ultimately unbitter, cynical smarts. If he’d wanted to, surely, he could have knocked out the rom-coms like a pre-McConaissance, naked bongo-smashing Matthew McConaughey. Maybe Rudd got lucky in that he never had one break out big for him to trap him in that look. More likely, though, from what we would come to understand about our man Paul is that he was always a little too off to hold aw-shucks for too long. His adventures in rom-com, then, have almost been stealth, launched in good nature with one early iconic role, then nodded to, for nearly two decades, in a series of feints and jabs, with heavy satire, confused sexual orientation, and at least one meddling jerk of a ghost.

Part I: Becoming Clueless 

Compared with his latter-day output, Rudd’s struggling actor days are disproportionately entertaining. A proud Jew from Kansas City via Passaic, New Jersey, Rudd paid rent for a while as a bar mitzvah DJ, and by the looks of it, he would have been psyched to keep that up forever.

That kind of pizzazz wouldn’t forever be relegated to the ballrooms of suburban Sheratons, though. He’d ping around, landing commercials (check him out, just super supremely geeked about his brother’s purchase of a Toyota Tercel), ill-conceived black-and-white shorts (please watch this thing called Picture Perfect to the end, because that’s when Rudd invents the selfie), and date rape–related movies of the week (Moment of Truth: Stalking Back!).

He got steady small-screen work playing a struggling filmmaker named Kirby Philby on the Sela Ward vehicle Sisters, which, with Wikipedia plot summaries like these — “By the final season Reed had divorced Kirby, lost custody of her daughter, and moved back to Winnetka where she eventually came to run a high-priced call girl ring” — I’m now regretting not paying more attention to. And he had a close call with a whole other TV trajectory, but Fox’s would-be Friends rival Wild Oats — on which, according to EW’s review, he played “dull guy Brian” — never went anywhere.

At the time, between shooting the show, which he hated, and the recent death of a friend in a car crash, he was moved to express some anger, which he did with giant cardboard drawings filled with obscenities. “[When] my mother saw that,” he told GQ, “I think she was very concerned and wanted me to come back home for a little while.”

And then, in 1995, came Clueless, such a time-and-place-defining cultural touchstone that primary members of the cast, despite whatever exciting business ventures they would subsequently engage in (DONALD FAISON WOULD LIKE TO POINT YOU TO HIS QUITE ACTIVE IMDb PAGE), feel forever stuck in that movie. Which means, strangely enough, that you might even forget Rudd’s in the thing.

Well you might, but a generation of mid-’90s teen girls — now flourishing ladies in their thirties, with disposable income and strongly held opinions — won’t ever. With one hell of a voice-over montage, young Cher Horowitz would instantly burnish the legend of Paul Rudd, approachable hot dude: “I mean, he’s just like this slug who hangs around the house all the time. And he’s a hideous dancer, I couldn’t take him anywhere. Wait a second, what am I stressing about? This is like, Josh! OK, OK, so he’s kind of a Baldwin, but what would he want with Tai? She couldn’t make him happy. Josh needed someone with imagination, someone to take care of him, someone to laugh at his jokes … in case he ever makes any. Then suddenly … I love Josh! I am, majorly totally butt-crazy in love with Josh!”

So we all are, Cher. So we all are.

Part II: An Object of Affection

The question can and should be asked whether Clueless is even a rom-com. I’d contend it at least contains a rom-com in it (official ruling from rom-com czar Juliet Litman: “High school movies are separate. It’s closer to Can’t Hardly Wait [cream of the crop] and She’s All That than Notting Hill and Sleepless in Seattle.”) What matters most for our purposes here: It established Rudd as a doe-eyed, alterna-romantic interest — the thinking girl’s man of choice.

And by the very next year, that’d be used against him. In Romeo + Juliet, he’s a sweet enough fellow in an astronaut suit, set to take Claire Daines’s hand in marriage — until she catches a mere glimpse of Young Leo through a fish tank, and forgets all about safe and sound. (Ah, well. At least he SPOILER ALERT?? doesn’t have to die. Probably ended up with a boring girl and lived happily ever after.)

At this point, years from being considered primarily a comedic actor, Rudd chases his ostensibly predetermined fate with a triple dose of “handsome but sexually irrelevant nice guy.” In 2000, he played Nick Carraway in a TV version of The Great Gatsby (it failed to make an impression, almost certainly due to lack of Lana Del Rey on the OST). The year before, in The Cider House Rules, he puts on quite the finely pressed Army uniform only to watch motherfuckin’ Tobey Maguire try to dance away with his girl. And the year before that, with The Object of My Affection, he even gave us a proper, full-on rom-com.

That the year is 1998 can be summarily deduced not only by the flagrant use of Sister Hazel’s “All for You” on the soundtrack (which, let’s be honest, still gets the goddamn job done) but by the confused sexual politics. Rudd is George, a young gay man in New York City; Jennifer Aniston is Nina, a young straight woman with a baby in New York City, who is in love with George and therefore intent on not letting him be gay? It’s a bit of a mess: Are you supposed to be, at some point, actively rooting for George to go straight? It’s harmlessly charming, though, and ever the yeoman, Rudd fulfills the stereotypical “gay best friend” role with aplomb.

Meanwhile, the sharp corners start poking out. Latter-day developments have rendered 200 Cigarettes an excessively weird, and therefore surprisingly memorable, ensemble for a bunch of reasons: Gaby Hoffman? Dave Chappelle? The rare double Affleck? Still, scruffy, sideburned Rudd, being interrupted from bathroom sex with Courtney Love by ex-girlfriend Janeane Garofalo, is a particular highlight. Also: “I’m just gonna go home and kill myself. You wanna share a cab?”

Wet Hot American Summer has already had Homeric epics written in its honor, and rightfully so, so for our purposes let us just recall Rudd, as Andy, finally channeling that beautiful inner jerk, teaching us the beauty of passive-aggressively cleaning up after yourself and coining what is still the most useful breakup line of our generation: “You taste like a burger. I don’t like you anymore.”

But halfway through the decade, he was still, fundamentally, a “nice guy.” That’d mean engagements both petite — Neil LaBute’s The Shape of Things, where he’s “nice guy getting made over by Rachel Weisz for reasons perhaps more nefarious than first understood” — and otherwise: For better or worse, going quirk for quirk with Phoebe on Friends was his most pervasive cultural moment since Clueless.

In 2005, he had a small role in his buddy Michael Showalter’s The Baxter,  a whole movie built on the skewering of rom-com conventions. The baxter is a made-up term for the nice guy who always gets left behind at the end for the true flame. (Greg Kinnear is the all-time embodiment, although Cary Elwes in Liar Liar is not to be trifled with in this regard: “Ooh, watch, yourself, it’s the claw! Oh, the claw’s coming atcha!”) Showalter’s character is a chronic nice guy fighting, desperately, in the days before his wedding, to not be baxtered again. Appropriately enough, Rudd himself was about to — HELLA DRAMATIC SLO-MO — throw off the yoke of nice-guy-dom.

Part III: Knocked Up Into Full Rudd

And that came with one great look. Anchorman was the predecessor, the introduction into the Apatow Family. But The 40-Year-Old Virgin was the proper juncture.

40-Year-Old Virgin is most certainly a romantic comedy, but it’s Steve Carell’s romantic comedy. Its greatness, though, is partly rooted in the elevation of the traditional roles of the near-psychotically selfless friend — po-faced blanks, the lot of them — into actual characters with internal lives. Cal, Jay, and David rep the same Smart Tech, but they don’t just want Andy to get laid because this movie needs a plot: In their own little ways, they’re channeling their dinged-up hopes and dreams through his (hopefully soon to be tarnished) purity.

Rudd, freshly brokenhearted — by the little-known Mindy Kaling! — is a force of nature of sweaty regret, and his downward spiral is nearly a tactile thing. Scene to scene, his dishevelment blooms and glows, until he ends up where we’re all, eventually, ending up: in a video-game chair wearing tracksuit pants and flip-flops and a T-shirt depicting his own mustachioed face. It’s almost like Andy from Wet Hot American Summer grew up, got a real job, convinced himself he was happy in denial, then snapped sharply back to his teenage-punk sadness. Still, though, there is love in him. “Remember that time, ” he coos, running into Kaling at speed dating, “and you cried in my arms? Let’s go to Paris. I wanna take you underneath the Eiffel Tower and make love to you.”

https://www.youtube.com/watch?v=PKPn-RFmWG8?t=29s

Over the next few years, taking back the no. 1 spot on the call sheet, Rudd knocked out some near proper rom-com leads. In little-seen The Oh in Ohio, he carries some raffishness (and an inappropriate relationship with Marisa Cooper!); in I Could Never Be Your Woman, he reverted back to his old happy-go-lucky ways — this is Rudd, in full bar mitzvah mode — to make Michelle Pfeiffer love life again. Over Her Dead Body, though, is the champion curio here.

First of all: Lake Bell actually gets a shot at lead status, and if there were any justice in the world, she would have gotten 10 more before becoming perennially underrated. Second: Eva Longoria — billed in the trailer, oh so beautifully, as Eva Longoria-Parker — plays an asshole ghost who won’t let her ex-fiancé move on with his life. How did we let this movie disappear from our lives? Why are we not talking about Over Her Dead Body with our friends and loved ones right now?

Once again, though, it was in a supporting Apatow role that he would attain Full Rudd. In Knocked Up, while standing in for Judd, Paul plays Pete, a well-off white American male with a beautiful family who still can’t fully shake a certain malaise. Caught outside his secret fantasy baseball draft, still convinced he’s authorized in his quiet rage, it all comes to a devastatingly illuminating point. “What’d you do last Wednesday night when you said you went to see a band?” Leslie Mann asks. “I went to see Spider-Man 3. With work and the kids, sometimes I need time to myself.” “I need time for myself, I want time for myself, too,” she answers, in quiet desperation. “I like Spider-Man.”

“As I’ve lived longer now, experienced more things, some of the optimism and wide-eyed stuff, it just gets beaten out of you,” Rudd has said. “It just does.”

Part IV: Bromance Is Still a Kind of Romance

A quick aside, into the bromance. Throughout Hollywood around this time, the form upends the rom-com, although the conventions are fundamentally the same: person meets other person, they don’t get along, they do get along, they don’t get along, they get along forever. Role Models is considered a more minor entry in the canon, shaped more in the About a Boy mold, in which the (totally non-questionable!) relationship is between a man and the small child who will help him truly grow. And you might have forgotten, but it’s pretty great, ably juggling the world-beating precociousness of Bobb’e J. Thompson (who, should someone be checking on him right now?) and a LARPing finale. I Love You, Man, though, is the one bromance we’ll send into outer space. As Peter Klaven, the sweet dweeb in chrysalis to ballsy man, Rudd lives out a slight echo of his career arc; meanwhile, Jason Segel becomes the dude we all want to almost ruin our lives. Hey, let’s listen to “Limelight” 17 more times!

Part V: Coming Together

Another decade, another string of rom-coms reminding us Rudd was never meant for straight-on takes on the genre. How Do You Know had all the bona fides — junior America’s Sweetheart Reese Witherspoon, James L. Brooks, the totally correct rendering of Owen Wilson as a doofy relief pitcher — but never coalesced right. Wanderlust was The Object of My Affection reunion the streets were begging for, but is now totally overshadowed by the eternal love of Justin and Jen. And by rights, Admission — Fey and Rudd? Fey and Rudd?! — should have been the one. It, as well, came and went.

The big swing, though, was This Is 40. On paper, a feature-length take on Pete and Debbie’s Knocked Up story seemed like a no-brainer. But over the 134-minute running time, the charm soured, until it became almost impossible to ignore that we were watching rich people complain about some rich-people shit. (The question of whether they’d be able to afford their mansion particularly grated.) Paul Rudd, though, as always, was Paul Rudd — the kind of guy we’d happily take a whiskey-fueled time-machine ride with any damn day of the week.

All things considered, is it any surprise we’d get the genre satire They Came Together? A lifetime of flirtation with the form has led us here: to Rudd spending two hours taking the piss. The proper rom-com is a special, delicate thing, its sweetness/cynicism balance carefully calibrated. But Paul Rudd was never meant to be Tom Hanks. He was always a little too sweaty.