We need to talk about Amy Heckerling. I know this is a post on Greg Kinnear in Loser but I need to start with the film’s director. A rising star in the 80s & 90s, Heckerling was the chief example of a successful female director in Hollywood. Her star blazed into existence in 1982 with Fast Times at Ridgemont High , a film that overcame the death sentence of “limited release” to become an iconic teen movie and launch Sean Penn’s career. Within the next several years, Heckerling directed Johnny Dangerously and National Lampoon’s European Vacation. She started writing her own scripts and made Look Who’s Talking. This “talking baby” comedy grossed so much money ($297 million) that it achieved two hallmarks of success: (1) the studio was sued by student filmmakers for plagiarism and (2) Michael Scott referenced it in The Office.

The notion that Heckerling needed reference material for her scripts (plagiarism or not) applied to her next two original movies: Clueless in 1995 and Loser in 2000. Since I’d never seen either of these movies before this post and Clueless is an all-time classic that just turned 25, I watched both. “As if” I need to discuss Clueless: it’s Heckerling’s most iconic American teen movie, and arguably the best movie adaptation of a Jane Austen novel. It transposes “Emma” to wealthy, culturally-isolated teens in Beverly Hills in the 90s. The movie slaps, featuring witty mile-a-minute dialogue, jammed with 90s references & songs, and launching the acting careers of Alicia Silverstone & Paul Rudd. Beyond this, Clueless portrays teenagers with relatable realism and creates sympathy for the posh, sheltered life of Silverstone’s Cher. It’s not so much that Cher doesn’t want to be selfless, but that her limited perspective hinders her.

A complete 180 from Clueless, Loser was a major flop that started the rapid decline of Heckerling’s career. There are many reasons Heckerling’s star faded, explored in this brilliant article, but I’m specifically interested in what went wrong with Loser. The movie checked the same boxes as Clueless and on paper should’ve been a success. Heckerling wrote the script, again adapting a classic work (The Apartment) to a teenage setting. She littered the mile-a-minute dialogue with pop culture references and stuffed the soundtrack with late-90s bangers. She even cast the two stars of the hugely-successful American Pie as her leads. But the comedic beats don’t land and the movie’s darker themes are hard to swallow. Let’s dig deeper.

Loser (2000)

If Clueless sympathized with clueless rich kids, Loser sympathized with smart poor kids trying to “get lucky” like the rich kids. Jason Biggs plays a small-town midwest boy headed to the big city (aka NYC) for college. (In a brief cameo, the always-wonderful Dan Aykroyd plays Jason’s dad and says the word “skosh.” Inspired, I added “skosh” to my vernacular and my wife was unamused). Arriving at college, Biggs’s main motivations are to be polite, make friends, and study hard to keep his Regent’s Scholarship. He also lacks fashion sense, wearing the same winter cap & coat every day.

Jason Biggs is so polite, he’s an unfashionably-dressed doormat. Photo Credit: Columbia Pictures.

Unsurprisingly, Biggs fails to fit in. He’s out-of-touch with big-city mannerisms like fist bumping, studies all the time, and his teetotaling ways are repeatedly mocked by his three roommates. One day, Biggs falls down the stairs entering his English Literature class. While the class laughs at him, Mena Suvari offers him ice for his injured knee. Because she’s the first person to be nice to him, Biggs is instantly attracted to Mena.

As we learn her backstory, Mena is also a “fish out of water” from a poor background. To pay her way through college, she waitresses at a local strip club (and when she’s fired looks for similar sordid jobs). She’s “dating” her English Literature professor, Greg Kinnear. For obvious criminal reasons, Greg wants to keep his hookups with Mena under wraps. He lets her come to his apartment for sex and maid-like services while stringing her along with false promises of love. It’s an uncomfortable & unfunny sideplot.

Mena Suvari goes for the stereotypical 90s goth aesthetic. Photo Credit: Columbia Pictures.

Meanwhile, Biggs’s roommates tire of his loser ways and evict him. Biggs moves into the large utility closet of a veterinarian clinic (because that’s a real thing that happens?!). Before long, Biggs’s ex-roommates are banned from having alcohol in the dorm and convince Biggs to let them throw a rager at the vet clinic. The night of the rager, Biggs invites Mena to an Everclear concert (remember them?!). She agrees to meet him there but instead goes to the rager where she’s slipped date-rape drugs by Biggs’s ex-roommates. Other party “festivities” prevent her from being sexually exploited, but Biggs later finds Mena in a comatose state and rushes her to the hospital.

Mena’s emergency contact is Greg, but he denies knowing her when called. So when she’s discharged from the hospital, Biggs brings Mena back to the vet clinic to recuperate. The two start to hit it off and bond over helping cats give birth. But Mena’s still convinced Greg loves her and eventually goes back to him. Meanwhile, Biggs’s ex-roommates discover Mena’s secret relationship, transfer to Greg’s class, and blackmail him for good grades. Biggs learns his former roommates are still slipping date rape drugs to girls and “stands up” to them by swapping their drug stash out for identical-looking placebo drugs. Eventually, Biggs learns Greg is sleeping with another student but doesn’t tell Mena. By chance, Mena overhears Biggs talking to his dad on the phone and learns that he likes her. She also (finally) realizes Greg is just using her when he insists on a formal makeover to invite her to his family Thanksgiving as his “teaching assistant.” Mena leaves Greg and the movie ends as she kisses Biggs.

There aren’t many pictures of Greg in Loser on the internet. That’s a good thing, let’s forget this role. Photo Credit: Columbia Pictures.

There are so many reasons this movie was a flop. Let me highlight three:

  1. Biggs is the wrong central character to use to explore mature themes like student-teacher relationships and date rape. He’s nice to the point of being a doormat. He (but really the script) mistakes caring for people with kind acts and conflict avoidance instead of looking out for his “friends’s” best interests and reporting criminal activities.
  2. The movie isn’t funny. The dialogue lacks the “As If” one-liners of Clueless and both Biggs and Mena are competent but unfunny. It’s hard to laugh when the only remaining jokes are pop culture zingers told by a teacher sexually exploiting his students.
  3. The plot is unnecessarily dragged out. This movie ends the instant Mena realizes Biggs is better for her, which feels rushed until you realize there’s nothing more to add. This begs the question why we needed any of the plot points after Biggs saves Mena from the rager.

The Grossest Greg

After 1998’s You’ve Got Mail, Greg went on a series of six movies playing narcissistic, slimy characters. In the “Greg Kinnear Character Universe,” it’s like the well-intentioned Frank Navasky was slighted so bad that his revenge extended for six reincarnations. There was the self-absorbed superhero in Mystery Men, the office lothario in What Planet Are You From?, the sexually exploitive teacher in Loser, the narcissistic soap opera star in Nurse Betty, the murderous fiancĂ© in The Gift, and the charming playboy in Someone Like You. On the one hand, Greg was cast in these roles because he excels at playing selfish, prideful, and insecure characters. Some of these movies mark his best performances. On the other hand, if Greg played this character type in perpetuity then I wouldn’t be writing this blog. The three “comedies” where Greg’s sliminess skews sexual have plot points that follow suit and were complete flops.

Greg and Twink Caplan aka Clueless’s epic Miss Geist on the set of Loser. Photo Credit: Columbia Pictures.

Greg certainly brings energy and decent acting chops to Loser. He displays quick witted arrogance as he berates his students for watching Leno instead of reading Kafka. His growing desperation is mirrored in nervous body language and speech when he’s blackmailed by his students or Biggs catches him romancing another student. Beyond this, many of his scenes with Mena are peak ‘Asshole Greg.’ While their entire relationship is Greg stringing Mena along, there were two ‘Asshole Greg’ scenes that stood out. In one, Mena prepares tea as Greg instructs (plunge the tea bag six times, squeeze in half a lemon, add 2.5 teaspoons of sugar) but brings it to him in a mug. Greg channels his best prima donna and responds, “Not in a mug. It needs to be in a cup with a saucer. [Pause]. Please.” In the second scene, Greg “surprises” Mena by scheduling a complete makeover to change her goth look to a formal one for his family’s Thanksgiving. Throughout it all, Greg adopts a perfect air of flippancy as he dismisses her objections.

Even with Greg’s range and energy, there were still a handful of scenes where “flirty Greg” took Mena to bed. It’s these scenes that are extra-uncomfortable and make me want to forget about this performance entirely. In sum, I really don’t know why Amy Heckerling thought the darker themes in Loser would make for a comedy as successful as Clueless. I assume part of this was adopting the plot of The Apartment and another part was sending a bigger message about date rape. Analogous to Clueless sending a bigger message about humanitarianism. But I also think Heckerling is fascinated by romantic relationships with a large age gap, as this theme continues in her equally unsuccessful next movie (I Could Never Be Your Woman).

I’ll end with the Kinnear Meter and no summary, since this post was long.

Pretending his sexual partner was age-appropriate, Greg’s performance in Loser was fine.

Next-Up: The Red Sea Diving Resort as we near the end of this project.

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