A Threat to Masculinity: ‘Tomcats’ and ‘Buying the Cow’

In the early 2000s, Jerry O’Connell starred in two movies: Tomcats (2001) and Buying the Cow (2002). Both focused on marriage phobic guys played by O’Connell finding and settling down with the woman of their dreams. Throughout the film, much of the humor focuses on male sexual and emotional anxiety.

Warning: Spoilers Ahead

Comedies at the Time

In the podcast “How Did This Get Made?”, Crocodile Dundee in Los Angeles (2001) screenwriter Matthew Berry explains that The Farrelly brothers’ There’s Something About Mary (1998) became the big hit comedy around the time these movies were made. A lot of what got sold and produced were similar types of comedies.

Something about Mary is a very specific type of comedy. It revolves more around large comedy set-pieces. The film opens with a flashback with its stars in ridiculous costumes and wigs. In this scene, the hero of the movie (Ben Stiller) gets embarrassed by a sexual mishap in front of his prom date (Cameron Diaz). Years later, Stiller still pines for Mary and decides to go find her.

Along the way, he meets an assortment of absurd characters through a convoluted plot. This includes a sleazy private eye (Matt Dillon) and a freakish best friend (Chris Elliott). Over the course of the movie, all the guys who love Mary pile up in absurd ways. In an interview, the Farrelly brothers said that they wrote it purposefully so the audience would not know if Ben Stiller and Cameron Diaz would end up together.

Perhaps what many filmmakers remembered the most were Mary’s bad taste and gross-out sequences. In one sequence, Stiller gets mistaken for a homosexual and a murderer. Another sequence has Diaz mistaking Stiller’s semen for hair gel. Similar sequences happen in many of the O’Connell movies. However, while they borrow many of the same gags, the O’Connell movies do not have the same anarchic raucous plotline or energy.


After their first friend gets married, a group of guys make a bet. The one to stay single the longest wins the whole pot.

7 years later. In need of money, Michael Delaney (O‘Connell) must marry off his final single friend in order to win a large pool of money. This proves difficult as his best friend is misogynistic womanizer Kyle Brenner (Jake Busey).

In order to do this, he enlists the help of Natalie (Shannon Elizabeth), a woman Kyle jilted who wants revenge. However, things go wrong when Michael actually falls for Natalie.


In Tomcats, the main threat is to the bachelor lifestyle of the lead characters. In this film, the worst thing that can happen is for a man to settle down to the exhausting responsibility driven lifestyle of marriage.

Whenever the film presents a happy union, it is usually in terms of them liking having sex together. The film literally measures Michael’s love for Natalie based on how much semen he can produce masturbating to her. However, for all the sexuality in the film, very little of it is actually titillating. Most of it comes across as anxious and absurd.

The film tends to present almost all the men who are not threatening as freakish. There is no real base-line character to measure the sanity of this world. Similarly, women either tend to look like supermodels (multiple models whole posed for playboy appear in this) or be completely unattractive. The film presents the opposite sex as either a threat to its lead character or somebody to shame him.


Tomcats opens on a cartoon of an anthropomorphic dog and cat competing for the affections of human women. All of the women are very sexually attractive. This sets up the absurd tone but also makes sense since Michael is sort of a cartoonist. The film takes place mostly from Michael’s perspective. The film rarely delves into another perspective (especially a female perspective) unless the plot needs it or it makes another joke.

Tomcats exists in a cartoonish universe, to the point of Michael literally getting electrocuted without any serious physical consequences. Along with the cartoonish style, Tomcats also parodies many topical movies, including the rose petal scene from American Beauty (1999) and the iconic rock climbing scene in Mission: Impossible 2 (2000) complete with doves to suggest the style of M: I-2 director John Woo.

From the over the top sound effects and acting to the heightened color palette, nothing exists in a grounded sense of reality. Every scene is about gags and jokes. The film ends with bloopers and outtakes showing how fun the film was to make.

The Creative Team

Director Gregory Poirier came up with the idea for this movie when he was told about a similar pool of money. Poirier had written in the industry for 10 years. His most successful films up to this movie include the racial drama Rosewood (1997) and additional material for The Lion King 2: Simba’s Pride (1998). This is his only film as a director.

This is also the first film of producer Joe Roth’s newly formed Revolution Studios.

The Protagonist

Michael does the color for the Sunday Garfield strip but hopes to branch out into more. He leads a pretty successful single life as a single bachelor. As a cartoonist, he draws sexually suggestive cartoons.

Besides being a cartoonist, Michael’s main defining character trait is his aversion to commitment after witnessing his friend get married at the age of 19. The film introduces him hyperventilating and promising that he will never get married. By the end of the film, all of that will change.

At the beginning of the film, Michael and Kyle make a pact to have sex with all the women on Earth. When Kyle announces his engagement, Michael has a dream about trying to have sex with as many tokenized women around the world and being completely overwhelmed by them.

The film seems unsure how it feels about Michael. A lot of the time he seems like the butt of the joke, but sometimes the film wants the audience to truly sympathize with him.

The Love Interest

Natalie begins the film as a beautiful ephemeral figure before the film presents a much darker character. When Michael first sees her after the wedding, she is dressed like a hooker on a street corner. It turns out that she is an undercover cop and Michael’s comments land him in a tough interrogation. She refuses in front of her boss but then finds Michael. She agrees to do it because Kyle took her virginity then abandoned her with a roll of quarters. Now she wants revenge. Michael enthusiastically agrees.

Over the course of the story, Natalie falls under Michael’s charm. However, most of their interactions have her treating him like the manchild he is. This includes her feeding him sushi-like an infant and telling him to quiet down on a stakeout. Even the sweet scene where they play mercy feels like something teenagers would do. Throughout the story, Natalie feels like more of an adult than Michael does, making the romance between them seem insincere and unnatural.

About halfway through the story, Natalie feels unsure about what to do with her feelings for Michael. After a discussion with her police partner (Bernie Casey) during a shootout, Natalie decides to challenge Michael by pretending to fall for Kyle. After dressing up like the epitome of a woman leaving, Natalie dresses up like a woman in an old melodrama. Throughout the rest of the story, the film separates Natalie from Michael except for a fantasy sequence.

Natalie does marry Kyle, allowing Michael to get the money. On their wedding night, she hits Kyle in the face with a roll of quarters, runs off, and annuls the marriage. When Michael hears about this, he meets with her, reconnects, and marries her.

The Best Friend

Kyle Brenner is a straight-up despicable character. His views about women are regressive and misogynistic in any universe. He gets a blowjob from one woman while talking to her sister on the phone, has sex with a Catholic school girl as she vomits out of her car window, and hates a certain shade of lipstick because it’s impossible to get off his penis. Most all of the women Kyle is with are presented as empty-headed sex objects of no real substance. This includes a woman Kyle runs over at a golf course and a bachelor party full of strippers.

None of the other characters in the story seem to like Kyle as much as they seem to tolerate him. Michael finds Kyle’s relationships with women repulsive when he sees him. When Michael thinks that Natalie has fallen for Kyle, he literally refers to him as the devil. The film also never presents a reason why Michael is friends with a guy if he finds him so despicable. Natalie seems straight-up repulsed by Kyle rather than somewhat attracted.

In the story, Kyle experiences a literal threat to his penis when a urologist (David Ogden Stiers) finds out he has testicular cancer. The doctor removes his testicle, but Kyle wants it back. This leads to a sequence where Michael tries to retrieve the testicle, only to have the urologist ironically eat it. Michael instead replaces it with a walnut.

Solution to Kyle’s Story

After Natalie tells Michael she has fallen for Kyle, Michael decides to sleep with the first woman he sees. This leads him to a mousy librarian (Heather Stephenson). The film makes her as wholesome as possible (she lives in a house with a white picket fence and drinks hot totties) before revealing a more threatening sexual nature. During this whole sequence, Michael is afraid for his physical safety. What once seemed wholesome has now been turned on its head. Even her sweet grandma (Marnie Crossen) comes in dressed in all leather. This sequence became a big part of the marketing.

The story comes back into play at the end when Kyle meets the librarian. She takes him back to her place. She is not impressed by him, so decides to bring her grammy in to peg him. This ends Kyle’s story on a joke before going into the credits.

Threatening Figures

In the story, the threatening figures tend to play into male anxieties or fears. However, the characters that seem threatening are not rarely cops or gangsters. Almost every attractive (and unattractive) woman Michael comes in contact with tends to be vaguely threatening, but some of them act differently. Like Natalie, they start out as nice before revealing darker dimensions.

Physical Threats

The plot happens because Michael meets a redhead (Amber Smith) in a casino he’s trying to impress by pretending to be a high roller. He does not realize that she is handling the dice for luck. He now owes 51,000 dollars to Hard Rock café fixer Carlos (Bill Maher), who will kill him if he does not get his money. Throughout the story, Carlos sends gangsters to repossess Michael’s possessions. However, the joke throughout the scenes is how cordial the whole experience is. Michael even tells them to drive safe when they leave.

Existential Threats

Tomcats presents women as an existential threat to Michael and his manhood. Michael compares the first real woman the audience sees on the screen to the devil. Throughout the story, women who seem perfectly innocuous turn out to be much more threatening.

The threatening male figures in the story tend to include ones who have long speeches about how horrible something is. The urologist who removes Kyle’s testicle makes a cruel joke about how horrible the procedure will be before laughing it and reveals its actually painless. Kyle’s uncle Murray (Garry Marshall) officiates the wedding and describes in graphic detail specific horrible situations that happen when one gets married.

Domestic Life

In the film, there are multiple wives. An implication at the beginning of the story is that all the guys have settled down and had kids, making Michael and Kyle seem more freakish to them. In a dinner scene with all of them, they are presented as openly talking about giving birth in the most graphic terms. This scene features Michael freaking out.

For the most part, the film presents children as a burden. Almost every child in the movie is very small and seen in terms of how they affect the sex drive of the parents and what they did to their mother’s vagina. The longest and most detailed scene with a child happens when a little girl (Dakota Fanning in her film debut) thinks Michael is a pedophile when he runs onto a playground dressed in his underwear and a stripper’s fur coat. It is a misunderstanding that leads to a cop chasing after Michael.

Married couple: Steve and Trisha

In both these films, the main group of guys has a married couple as friends. These characters serve as a foil for the wacky bachelor antics of the leads and provide a view into married life.

In this case, it’s the guy’s recently married friends Steve (Horatio Sanz) and Trisha (Jaime Pressley). The film makes Steve the lamest character and dresses him in the loudest and most colorful shirts possible.

Unlike Steve, Trisha seems more sexually active. The opening scene has Trisha slipping her father’s boner pills into wine to give the groom “a three-day boner.” The groomsmen drink the wine, giving the groom and his best men erections throughout the wedding.

Throughout the film, Steve suspects that Trisha is having sex with women after seeing her on tape with getting a topless massage from another woman. Throughout the film, he looks to catch Trisha in the act. This leads to a running gag of Steve seeing Trisha behind a silhouetted curtain with another woman doing something sexual. However, when he rips back the curtain, it is revealed to be completely innocent. This includes their maid Consuela (Sole Alberti) and his nurse Kelly (Brandi Andres). When Steve asks what Consuela actually does, she knowingly looks at Trisha.

In her final scene, it is revealed that Trisha is actually having sex with both the maid Consuela and nurse Kelly. Steve acts offended by Trisha until she acts Steve he wants to join them (which the other two women seem cool with). Steve rips off his clothes and jumps into bed with them like a mad man. Something that was suspicious the whole film becomes the fulfillment of a male fantasy.

‘Buying the Cow’

After getting a marriage ultimatum from his girlfriend, Los Angeles based graphic designer David Collins (O’Connell) panics and sets out on the search for true love. The rest of the movie focuses on David’s various misadventures in dating.


In Buying the Cow, the film’s sexual status quo is ideal. The worst thing that can possibly happen to its male characters is be mistaken for homosexuals, sexual deviants, or predators. Throughout the film, this happens over and over again.

The comedy in the story comes out of people playing the scenes in a more realistic manner. For the most part, there is a greater diversity of characters in Buying the Cow. Not every young woman in the film looks like a supermodel and not every older woman seems grotesque. Unlike Tomcats, there is no juxtaposition of the female characters. All the women in the story tend to be presented in a blunt manner.

The lead characters seem like the anti-heroes of the story. Most of what happens occurs because of the male leads doing utterly selfish and horrible things. Women do not seem to threaten as much as the uncertainty about them does.


Unlike the live-action cartoony nature of Tomcats, Buying the Cow is a much odder movie. At times, it aims to be sincere and say something meaningful about love. David’s relationship with his girlfriend is treated this way. At other times, the story plays out like a farce or screwball comedy, where misunderstandings pile up into more and more ridiculous situations. The film also does not really release the tension created by the more dramatic or more farcical elements. The characters all end the story pretty okay with each other.

Even more than Tomcats, the sexuality and nudity in buying the cow is not supposed to be that sexy. The largest amount of nudity comes from Ryan Reynolds trying to escape through a bathroom window.

Another big difference comes in the look of the movie, which has a much colder and sicklier color palette. Blues, blacks, greens, and purples permeate scenes. The scenes with warmer colors and beauty shots revolve around when the protagonist sees a dream-like woman.

The Creative Team

Co-writer and Director Walt Becker has made multiple films about male friendship. Becker made this film as his debut feature in 2000, but it sat on the shelf for two years when distributor Destination Films went bankrupt. Becker would become better known for another feature released that year: Van Wilder, which stars O’Connell’s star in this film, Ryan Reynolds. From there, Becker made two John Travolta movies that focused on male friendships: Wild Hogs (2007) and Old Dogs (2009).

Becker co-wrote the film with Peter W. Nelson. Nelson has a couple of associate producing credits on action films (including the Dennis Rodman vehicle Simon Sez (1999)), but this is his only writing credit.

The Protagonist

The film primarily focuses on David Collins’ quest to find true love in an uncertain world. He loves his girlfriend Sarah (Bridgette L. Wilson), but does not know if she is “the one.” While on a break from his girlfriend, he sees another beautiful woman (Scarlett Chorvat) and decides to pursue her.

At the beginning of the story, David has no problem, but his anxieties prevent him from being with his girlfriend forever. David’s journey involves him having to realize that there is no one special person that anybody is destined to be with. David has a speech in the middle of the movie comparing the uncertainty and opportunity of meeting the “perfect person” to rain. Sometimes it happens and sometimes it doesn’t.

Framing of the Protagonist

The film presents David as the romantic hero but presents every one of his choices as unequivocally wrong, traumatizing or strange. To women, he seems childish, freakish, and absurd. The film has him transformed in multiple freakish physical ways. A great example comes when David invites four women to a restaurant to see which one is his dream woman. When his plan comes to light, they beat him up. This causes a blood vessel to burst in his eye and for it to turn bright red. For almost every woman David pursues, there is a physical transformation that makes him appear odd and separates him from the audience.

The Love Interests

In Buying the Cow, there are two love interests: David’s girlfriend Sarah and the ethereal Katie Madison. Both these women represent different worlds to David.

Since David’s story revolves around him realizing that searching for a magical woman is not a good idea, the film presents visions of the perfect woman. Jonesy compares the myth of the perfect to a shadow and says that when they are actually given real features they become imperfect. The film then cuts to Sarah coming out from behind a silhouetted window.


In Sarah’s story, David is the “other guy” character she dumps. In a flashback scene, the audience sees what it is like after Sarah has disappointing sex with David. He immediately looks over and says, “hey, South Park is on.” This joke makes David seem childish.

Sarah opens the film by giving David an ultimatum (or as she calls it “a deadline”): marry her or end the relationship. She takes an assignment in New York to give David a time to decide. As the film goes on, Sarah and David slowly realize that they do not belong together. This includes a phone call where David asks why she does not just keep her job in New York as she seems happy there.

Sarah breaks up with him when she returns to LA to see him, only to have him go to New York. At the end of the film, Sarah has met another attractive guy. In an article for Variety, Destination co-head of production Brad Jenkel said that what made the movie interesting was that the female lead was actively searching for love as well.


The trailer presents David as a romantic dreamer who wants to find the perfect woman. However, it omits one critical part in favor of focusing on Ryan Reynolds’ part. That element involves David’s story about meeting a girl at an airport when he was 18-years-old and giving him her address. The girl Julie Madison (Erinn Bartlett) writes him back and he divulges his fantasy about running away and making babies with her. What David does not realize is that Julie is a very developed 11-year-old girl (in real life, Bartlett is older than Jerry O’Connell). The police show up and make sure everything stops immediately. Throughout this sequence, the film presents David as a goofy teenager with a very unflattering mullet.

Over the course of the story, David learns that his friend in New York, Tyler (Ron Livingston), is getting married to Julie. He goes and meets them at the expense of his current relationship with Sarah. Unfortunately, he learns that the story is much worse than he thought. Julie saw him as a dangerous stranger who accosted her in the airport (the film presents him as heavily sunburned with chapped lips). Julie actually threw the address away. Her 9-year-old sister Katie found it. Idolizing her sister, Katie wrote him. Her parents discovered this and called the police.

Solution to David’s Story

In the present, David has seen Katie at a diner. He wants to meet her but keeps barely missing her. Katie spends the film sitting in the diner circling personal ads. When David first sees her, the film backlights her so the audience knows that this is a special woman.

The film has a happy ending with David finding Katie but also sets up that this is the 9-year-old sister and that she was legitimately traumatized by the experience. Her sister says that she hates weddings because of the experience. The film ends without really addressing this story.

The Best Friend

David’s womanizing best friend Mike Hanson (Ryan Reynolds) gets introduced talking himself in the mirror before doing the tuck from Silence of the Lambs (1991). This is before David’s other friend Jonesy (Bill Bellamy) comes and gets disgusted by Mike’s display. Throughout the first act, Mike is presented as sexually insecure about his status as a man.

Like David, Mike has his own insecurities about finding the perfect woman. This includes Mike calling up Tyler at 4 in the morning to ask him how he found the perfect woman. Mike also talks about women as fish and “hooking a marlin.” Deep down, Mike wants to find a magical woman for himself too.

Things really heat up when Mike wakes up in a woman’s room. He thinks he might be gay after the effeminate roommate of his most recent conquest walks into the room. The roommate explains that Mike slept with his female roommate, but Mike does not listen to him. This leads to Mike believing her might be secretly gay.

Solution to Mike’s Story

Amy (Alyssa Milano) is a stripper who went to college with David and Mike. David had a relationship with her in college. When David runs into her again, he asks her how their relationship would have worked out. She says it would have lasted two and a half more days because she had to study for finals. The film sets up their later relationship by having Mike wondering if he could have gone out with her. This line sets her up as the woman Mike will end up later in the movie.

At the end of the movie, David brings Amy to Tyler and Julie’s wedding as a date. In his best man’s speech, Mike comes out, much to everybody’s horror. She does not believe Mike’s coming out and takes him over to the newlywed’s limo and makes out with him, only to have the Newlyweds and rest of the wedding find him.

Threatening Figures

Buying the Cow presents the threatening parental or respectable figures who fear for the safety of a child. For the most part, children appear very sparingly. Almost every scene with a child involves a misunderstanding where an adult believes that one of the leads is a pedophile. The children tend to be a little older than in Tomcats and innocent about what is going on.

However, in most cases, they are threatening because of a giant misunderstanding. A great example of this comes when a child mistakes a naked Mike for Spiderman after he climbs down. His father sees him, gets a gun, and starts shooting at him.  A smaller example occurs with Tyler, who gets angry as Julie describes her scary encounter with David. Tyler says that he would beat up “that guy” if he met him. In both cases, the man is completely justified within the story in behaving this way.

The Married Couple: Tyler and Julie

The film’s initial incident occurs when David freaks out about his friend Tyler getting married. Tyler is portrayed as a level headed nice man who absolutely worships the gorgeous Julie. She is the magical one.

The opening of the film has Tyler describing her over the phone as he pours chocolate syrup on her. Midway through the film, David learns that Tyler has decided to marry Julie Madison. Like Katie, the film mostly presents Julie as an ethereal figure rather than a full-fleshed character. The film also chooses to backlight her the same way it backlights Katie. The audience does not get to know much more about her than she is beautiful and marrying Tyler.


In both films, male anxieties fuel the comedy in the story. At the beginning of both stories, the protagonist fears commitment. Dating and the pursuit of women are a nightmare that the romantic hero must constantly confront. By the end of the story, the character will have committed to somebody, thus ending the nightmare.