The underrated sitcom My Boys made relationship games fun

The TBS sitcom My Boys, which aired from 2006 to 2010, was crafted as a kind of flip side to Sex And The City: It also featured a young female protagonist navigating life and love in a major metropolis surrounded by her pals, but was set in a different city and had a different sensibility. Instead of the quintessential fashionista, My Boys lead P.J. (Jordana Spiro) was a Chicago sports writer who mostly hangs out with men, like her brother Andy (Jim Gaffigan); her best friend, Brendan (Veep’s Reid Scott); and her on-and-off crush, Bobby (Kyle Howard); along with poker buddies Mike (Jamie Kaler) and Kenny (Superstore’s Michael Bunin); and super-girly girlfriend Stephanie (Kellee Stewart). Her voice-over narrations pontificated about relationships like Carrie Bradshaw’s did, but were steeped in sports analogies, usually baseball-related.

Over the course of four seasons, My Boys grew to resemble Sex And The City less and more a hangout comedy, like an organic, laid-back Friends (the single-cam format over the multi-cam helped in that regard). The cast had enviable chemistry across the board, with wisecracking one-liners and ad-libs that cemented the feeling that you were watching an actual group of friends. Like P.J., series creator Betsy Thomas had attended Northwestern University in Evanston, so most of her exclusively North Side references (especially Cubs-related) were spot-on. Mentioning Second City entities like the Billy Goat Tavern, Harold’s Chicken, and Water Tower Place, or seeing Brendan sport a T-shirt featuring the logo of popular music venue Metro, helped viewers feel more familiar with the Chicago-set (but L.A.-filmed, for the most part) series, unlike Chicago sitcoms that had little to do with their hometown (looking at you, Happy Endings). The gang’s hangout, Crowley’s, was even based on the Wrigleyville bar Guthrie’s, down to the board games on bookshelves and the checked tablecloths.

My Boys never had a groundbreaking will-they/won’t-they moment or an earth-shattering breakup. The series’ event episodes involved rare actual Chicago settings and not much else (give or take P.J. and Stephanie’s trip to Italy and the gang’s trek to a glamorous ranch out West). But for 49 episodes, the series always delivered an entertaining half-hour; it was a warm, welcoming hangout among friends, the constant refrain of “Who needs?” leading to yet another round of domestic beers for the table. While P.J. had a plethora of suitors across the show’s four seasons, they never seemed as important as the core group. The true fun of My Boys was found in the endless asides and wisecracks thrown around the poker table. For example, when the gang discusses going to a place they’ve never been, Kenny suggests that Mike could visit “the company of a satisfied woman.” The zing is so good that Mike has to compliment him: “Hey, you got one! Did it feel good?” Gaffigan’s Andy usually had a couple superlative one-liners or two per episode, as when he pontificates about how some people “call fat guys Tiny or ugly guys Handsome.” Kenny: “What?” Andy: “You know what I’m talking about, Handsome.” When P.J. complains about her friend who just wants to “spa” and “club,” Andy replies, “I like your verbs that are things. I’m think I’m going to sandwich after I sofa here for a bit.”

To help My Boys succeed, the show entered into a huge product placement deal with Match.com, estimated at $1 million to $2 million, which made sense considering the show’s subject matter. The show was billed as “sponsored by Match.com”—a throwback to the early days of radio when shows were sponsored by Jell-O or Johnson Wax—while the product placement was woven into some storylines: “The Web site will be featured prominently in two episodes and play cameo roles in the rest,” said The New York Times. A 2007 Ad Age article reported that this attempt at seamless integration boosted both brands, leading to a “spike” at the dating site. It certainly helps explain not only the Match.com references but the show’s other prominent product placements, like a giant bottle of Coffee-Mate on a brunch table, or the frequent naming of beer brands.

Unfortunately, even that lucrative avenue for My Boys couldn’t overcome some scheduling shenanigans from TBS. Debuting on Tuesday nights, its first season was only supposed to have 13 episodes, but got combined with the next nine for one 22-episode season, followed by three much shorter nine-episode installments that ran around the summer months. The series moved to Thursdays for season two, then back to Tuesdays for season three, culminating in a death-march Sunday-night slot against more buzz-worthy cable shows like Mad Men for what would turn out to be its final season.

In honor of the 10th anniversary of My Boys’ series finale in September 2010, we offer 10 emblematic episodes of this fine sitcom. Seasons one and two are available free to view on Crackle (hey, Crackle is good for something!), while the final 18 episodes are available on DVD, but still worth seeking out. Who needs?

“Pilot” (season one, episode one)

The baseball analogies fly fast and furious in My Boys’ debut episode: We quickly learn that P.J.’s apartment (yes, a ridiculous spread considering her Sun-Times sports reporter salary) functions as the gang’s clubhouse. Utility players Kenny and Mike are like infielders. (In a testament to the cast’s real-life friendships, Kaler and Bunin followed My Boys with a sports-themed YouTube series, On Deck With Jamie And Mike.) P.J.’s brother, Andy, who only stops by for occasional visits now that he’s married and has a kid, is the relief pitcher. The gang’s habitual team sport is a weekly poker game. But it’s newcomer Bobby who makes the biggest impact right away, as his chemistry with P.J. is palpable. Best of all, he likes her for all the right reasons: her expert softball coaching skills and childhood baseball card collection. Things take an unfortunate turn, though, when Bobby gets freaked out when P.J. is as sexually aggressive as he is (tarnishing some of his adorable luster), derailing the pair’s connection for a good long while—but as we will see, not permanently. Points off for poker-night pizza that’s not cut in the traditional Chicago tavern stye, and mentioning pandas at the Lincoln Park Zoo (there aren’t any).

“Baseball Myths” (season one, episode 13)

An episode that revolves around Andy’s birthday is automatically superior, because it not only offers more Gaffigan but also casts his charming real-life wife, Jeannie, as his wife in the show. Andy has always played Meredith up to the gang as a shrew who gets mad if he stays out too late. Turns out, she’s the nicest person on earth, and Andy has been using her as an excuse to go home early, because he’s tired. The episode also features the gang’s special private visit to Wrigley Field for Andy’s big day. On top of that, “Baseball Myths” elaborates on the previously unaddressed chemistry between P.J. and Brendan. They reveal that they made out once in college, shocking their group of friends, and by the end of the episode, they make out a second time. In most other sitcoms, this would make for a tired love triangle between P.J., Brendan, and Bobby. Instead, My Boys conquers the nearly-impossible-to-pin-down perfect platonic relationship. P.J. and Brendan are that couple who really do love each other too much to ever date, at the risk of ruining their all-important friendship. Thanks to Scott and Spiro’s believable chemistry, their non-romantic relationship makes perfect sense.

“Douchebag In The City” (season one, episode 19)

This episode, co-written by Thomas’ husband, Adrian Wenner, is one of the greats. “Douchebag” confronts the Sex And The City comparisons head-on when P.J.’s old college buddy Lyssa (a pre-Rectify Abigail Spencer) visits from New York with three very familiar pals (P.J. continually tries to tamp down the double entendres from the Samantha doppelgänger). Meanwhile, Brendan has turned into a total douchebag after being named one of Chicago’s most eligible bachelors, a status punctuated with a very funny cameo by an uncredited Ryan Reynolds as Brendan’s new pretentious friend Hams. The episode captures how some New Yorkers look down upon Chicago (Lyssa and her friends have a special guidebook to steer them toward the most New York attractions in the Second City) while also exploring how even the best of friends may grow apart after a while. Lyssa may be a lost cause, but P.J. is determined not to lose her now-fame-obsessed roommate—who name-drops local celebs Billy Corgan and Jeremy Piven—culminating in an epic douchebag intervention to get Brendan to return to his usual affable, low-key self (Kenny: “When you tried to get me to buy the new Fergie album, it made me feel so lonely”).

“Rome, If You Want To” (season one, episode 22)

On the surface, “Rome” is primarily about P.J. juggling various romantic interests (a cute botanist, an ex-Cub, and a college fling played by none other than Jeremy Sisto) before her trip to Italy, but it really stands as an homage to the city it’s set in. Propelled by an uncharacteristically spirited Andy, the gang makes a pact to spend a day visiting Chicago landmarks they’ve never seen before, even though Brendan is less than enthusiastic. A few of these attractions are in the Ferris Bueller vein—Mike takes them all to visit the Art Institute, and Kenny tries to conquer his fear of heights by visiting the Sears Tower—though Bobby offers a fun detour to Oak Street Beach. The group’s celebratory brunch is interrupted by Andy singing “Danke Schoen” to Brendan from the top of a tour bus. “Rome” shows the advantages that can come from exiting your comfort zone. (Although Bobby’s trip to Lake Michigan unfortunately nets him a rash, due to an algae outbreak.)

“The Shirt Contest” (season two, episode three)

Even the best of friends who hang out practically every day run out of things to talk about, so My Boys was constantly having the guys come up with ridiculous contests and challenges (see: the mustache-growing contest that starts in the season two finale and continues into season three). “The Shirt Contest” is one of the best of these. After Mike scoffs at the projects on Project Runway, he, Kenny, Bobby, and Brendan engage in their own make-a-shirt contest, with predictably hilarious results (Mike’s shirt doesn’t have a back; Kenny’s is a tablecloth). The shirt saga is so good that it knocks the A-story, P.J.’s failed attempt to write a book with Mets player Spike Upton, right out of the water. Meanwhile, Brendan loses his job and has to come to grips with the fact that his longtime love Wendy has moved on. Fortunately, P.J. comes up with the perfect, shirt-contest-related result to cheer him up.

“Jack & Bobby” (season two, episode eight)

One of P.J.’s most complicated suitors was Bobby’s brother, Jack (played by Twilight dad Billy Burke). Bobby enters into a ridiculously fast courtship with Elsa, Andy’s nanny, then decides to marry her to save her green card status. The gang travels to the Newman family’s expansive ranch in California for the wedding, where P.J. realizes that Jack and Bobby have some unresolved family issues. But the best part of the episode is just seeing everyone hang around in a different setting: a wine tasting, where they extrapolate about the special rules involved in day-drinking (pro tip: everyone pick a buddy to help prevent the deadly post-day-drink nap). It’s also enjoyable to witness the episode’s guest stars, like Christopher McDonald as Bobby and Jack’s lecherous dad, and Mimi Rogers as a cougar-ish wedding attendee who takes a particular interest in Mike.

“Decathlon: Part Deux” (season three, episode four)

The decathlon—an annual tournament wherein the friends challenge each other on the Crowley’s-stocked board games like Password and Kerplunk—first appeared in season one. This time, though, stakes are higher because new couple P.J. and Bobby are on a team together with Kenny, taking on Andy, Mike, and Brendan. The competitive P.J. quickly gets frustrated with the inexperienced Bobby’s moves during Operation (“Go for the spare ribs!”). When Bobby calls her out on it, resulting in their first fight, she atypically squelches her cutthroat nature, which frustrates him even more. The decathlon is fun just for the ancient Hasbro games involved (remember Don’t Break The Ice?), but it’s also a valuable early indicator of the solidity of P.J. and Bobby’s relationship: taking things step by step, learning more about each other as they go, without unnecessarily heightened breakups and makeups just for the sake of sitcom drama.

“Spring Training” (season three, episode nine)

In the season-three closer, the gang travels to the Cubs training camp in Mesa, Arizona, and the episode makes a convincing argument for why they all love sports so much. At spring training camp, anything can happen: like a rookie accomplishing the rare feat of hitting a cycle (a single, double, triple, and home run all in the same game). Free to be just fans for once, P.J. and her pals ably convey that from-the-stands excitement at the start of a new season, when possibilities are endless. Brendan might even stop shopping for girls at the “crazy mall,” as P.J. puts it, when one of his many dalliances gets him in hot water with then-Cub Mike Fontenot in a cameo. And after keeping their relationship under wraps for an entire season, Kenny and Stephanie are spied by P.J. and Bobby at the end of the episode, effectively outing them as a couple.

“Addition By Subtraction” (season four, episode one)

Season four had a rocky start due to the departure of Jim Gaffigan, who left the show to focus more on his stand-up. My Boys covered the loss by offering an overdue origins episode, showing the first time the friends encountered each other. The episode is made classic by the two versions of Brendan that Reid Scott portrays when Stephanie and P.J. meet: from a super-cool grunge rocker to super-dorky frat guy. Kenny, unsurprisingly, was a waiter at Ed Debevic’s, the now-closed Chicago diner that infamously had its waitstaff insult its customers. Bobby and P.J. had an encounter even before their meet-cute in episode one. Gaffigan is definitely missed, but the loss is mitigated by the cast’s spot-on grumbly impressions of him: “These ice cubes make the scotch taste like freezer.”

“My Men” (season four, episode nine)

Knowing that the writing was on the wall for the probable end of the show (its cancellation was announced soon after this episode aired), series creator Betsy Thomas wisely wrapped everything up in a satisfying fashion. Kenny commits to Stephanie and decides to move with her when she gets a job offer in London. Mike steps up and gets married to Andy’s neighbor (the always-fun Rachael Harris). Bobby plans on law school as he and P.J. remain living together. Best of all, Brendan buys the gang’s shuttered hangout Crowley’s, ensuring that the group’s Old Style-fueled nights will continue, while also giving him the grown-up career he’s been lacking. And P.J. makes a major career decision when she realizes that she values her great life over the demands that a more challenging job would give her. As all six of the main characters take a major step forward in their lives, the tellingly titled “My Men” was a fine way to wrap up this underappreciated series.