Pop culture obsessives writing for the pop culture obsessed.

With so many new series popping up on streaming services and DVD every day, it gets harder and harder to keep up with new shows, much less the all-time classics. With TV Club 10, we point you toward the 10 episodes that best represent a TV series, classic or modern. If you watch these 10, you’ll have a better idea of what that series was about, without having to watch the whole thing. These are not meant to be the 10 best episodes, but rather the 10 most representative episodes.

It’s become a somewhat common occurrence for TV series to be cited as breaking ground for minority groups, be it The Cosby Show or Norman Lear’s socially conscious comedies. But few of those TV shows are as maligned by the groups for which they ostensibly broke that ground as Will & Grace. This is a show that got name-dropped by the vice president of the United States as a contributing factor to forming his opinion on gay rights, gay marriage in particular. Still, mentioning Will & Grace in mixed company can elicit any number of reactions about the show’s depiction of gay characters and whether it was “good” for the gay community. That’s a lot of pressure to put on any TV show, much less a traditional-in-tone, three-camera network sitcom that debuted in 1998, but that’s the plight for the only network show with gay lead characters in an entire era of network TV.


Creators Max Mutchnick and David Kohan produced the show for Warren Littlefield-era NBC, a network that was sitting pretty, particularly when it came to sitcoms, and could afford to take a chance on a show about a straight-woman/gay-man friendship (one based on Mutchnick’s own relationship with his best friend). Will and Grace were best friends since college, dated before Will came out of the closet, and have remained remarkably, often unhealthily, close. The tagline to the pre-premiere ad campaign was “They’re not a couple. They’re a couple of best friends,” so clearly, the idea from the beginning was that Will’s sexual orientation was going to be this show’s twist on the relationship-sitcom formula.

As the only gay lead character on network TV at the time (Ellen had just ended when Will & Grace debuted), Will Truman was both revolutionary and yet decidedly not. Eric McCormack was a straight actor, and despite the bulk of the jokes on Will & Grace being about gayness, Will’s defining characteristic was how unthreatening he was. Will was rebounding from heartbreak as the series began, and the show would often lean on this “unlucky in love” crutch with Will, which added up to a noticeably chaste lead character, certainly when compared to his straight sitcom contemporaries at the time. For as much as Will & Grace made it safe for “regular” Americans to be around gay men, at least in the fictional realm, the Will character grew to be a symbol for the neutering of gay TV characters for public consumption.


The flip side of that coin was Sean Hayes’ Jack McFarland, who came screaming into the American consciousness all bitchy quips and flailing arms. The femme yang to Will’s yin, Jack was about as over-the-top a TV character as existed at the time, and with his primary counterpart, Megan Mullally’s Karen Walker, he provided the show with its campy soul. But Jack was also a very easy target, and one that the show had no trouble making a very frequent butt of the joke. This marks a tough balance: Sitcom characters were meant to be laughed at, but the frequency with which Will & Grace returned to the well of nelly—usually Jack flailing about—for its (predominantly mainstream and straight) audience had a touch of the minstrel to it.

This leaves one gay lead who’s a eunuch and one who’s a dancing fairy. As the series itself suffered a drop in quality about halfway through its eight-season run, the program became far more frequently an object of ridicule than of revolution. And that’s not even getting into its latter-season addiction to high-profile guest stars, from Madonna to Janet Jackson to Jennifer Lopez, each one less essential than the last. (That Martina Navratilova cameo, though. That one’s gold.) If Will & Grace was groundbreaking for anything, it was the idea that gays could lead middlebrow, unchallenging, past-its-prime sitcoms just as well as straight characters.


But now, seven years after its final episode, it becomes easier to wonder if the burden of sole representation didn’t lead many viewers to be too hard on Will & Grace, Will and Jack in particular. Contrasted with a current media landscape that sometimes attempts to maintain that gayness doesn’t matter (the “Max on Happy Endings is a gay who doesn’t even seem gay!” school of thought, for example), Will & Grace wasn’t going to let viewers forget they were watching a gay sitcom, whether it was via Cher cameos or Fire Island inside jokes or Karen Walker being America’s next drag superstar long before RuPaul’s Drag Race.

More importantly, this was a show that was well aware of the character types it was sending out into the world and would often interrogate those characteristics within the series. The best episodes of Will & Grace had a sense of the characters’ place in the entertainment landscape and would wrestle with how the show wanted to portray them. Will’s tendency to tone himself down, Jack’s friends being embarrassed by him, Will and Grace’s unhealthy attachment to each other—these “flaws” in the fabric of the show were often complications that seemed to want to address something bigger. The realities of a 22-episode network TV schedule meant that those moments of self-critique were lost amid a show that was not afraid to rest on its screwball laurels, but in picking the 10 episodes that represented Will & Grace at its absolute most essential, those qualities are a bit more apparent.


“A New Lease On Life” (season one, episode two): After a pilot that was occupied with moving Grace from her runaway-bride status (shades of Rachel on Friends, to be sure) back into the embrace of her gay best friend, the second episode focuses much more specifically on the codependent nature of Will and Grace. Those who observed that the title characters’ relationship grew toxic and unhealthy as the series progressed might be surprised to see how directly the series deals with that very issue, from the second episode of the series on. By episode’s end, Grace makes the choice to move in with Will, actively rejecting a more independent life, because this is the easier choice. Things still seem very young, with elements yet to be excised (Jack has a parrot?) and characters yet to fully coalesce. Karen, in particular, took a few episodes to find her voice, figuratively and literally, and Gary Grubbs is present in what would be a recurring role in the first season as a client of Will’s who is well-meaning, but still not 100 percent at ease with all the gay stuff; he’s called “Harlin” but might as well have been named “Audience Surrogate.”

“Will Works Out” (season one, episode 19): This is one of two Will & Grace episodes to feature a writing credit for Sex And The City’s Michael Patrick King. Fans of Two Broke Girls may be interested to know that this episode features fairly prominent use of the slur “fag.” As a series, Will & Grace threw around “fag,” “homo,” and “lez” in a way that other shows that were not produced by and about gay men wouldn’t dare, and it did so in ways that were not always terribly responsible. There was a definite air of “We can say it because we’re gay” about the show, which is not a rare sentiment. But “Will Works Out” actually confronted the terminology, thankfully not in a Very Special Episode, or a “this is why words hurt” fashion, but in tackling the sentiment behind it: Will is embarrassed by how effeminate Jack is. That Will Truman and Jack McFarland end up representing such polar opposites of gay representation on TV makes this kind of episode both necessary and all too rare. For any show about gay men in a world that is steadily allowing them to exist outside the closet, it’s important to investigate the self-policing that was (and still is) happening regarding butch, “masc,” and femme portrayals.


“Object Of My Rejection” (season one, episode 22): The first season finale drops one of its most sitcommy plot devices on the characters, as Karen’s maid Rosario (Shelley Morrison making her first appearance on the series) needs to marry a U.S. citizen or face deportation, and suddenly, there’s Jack, with no domestic ties or moral objections. The Karen/Rosario relationship is another case of Will & Grace getting away with a lot of offensive material (Karen is absolutely awful to her) due to the performances being so charming and funny and the unexpected heart at the center of their squabbling. They snipe, and they fight, but they can’t live without one another. The other half of the plot once again visits the codependency place for Will and Grace, as she wants to go back to her ex-fiancé, much to Will’s objection. After a mid-ceremony fight, an anonymous wedding guest asks why they’re so heated if they’re not married. Why indeed. Also worth noting: Karen’s Asian-inspired red dress at the wedding is superb.

“I Never Promised You An Olive Garden” (season two, episode nine): One of the constants in Will & Grace’s run is that Will and Grace are somewhat awful people. That tendency is on display in this episode, as the pair tries to ditch their boring New Jersey friends Rob and Ellen (the delightfully recurring Tom Gallop and Leigh-Allyn Baker) for the tragically cool downtown couple they meet at dim sum. Their hero worship of this American-yet-Eurotrash couple only makes Will and Grace look dweebier. But that’s the weak sister of the episode’s two plots. The scene that makes this episode top-10 worthy is when Jack accompanies Karen to a parent-teacher conference and ends up helping out a bullied gay kid. For as much as stupidity became Jack’s defining characteristic, there were moments like this where he stood out among the TV landscape as not only gay and proud, but also sissy and proud. That very characteristic would become a constant butt of jokes from Will and other characters, creating a mixed message at best, but just try and watch the scene where Jack and the boy bond over their ideas for one-man shows (followed by an invite from Karen to martinis at the Palm) and not smile.


“There But For The Grace Of Grace” (season two, episode 21): This is another episode that splits Will and Grace off from Jack and Karen, though the rare one where Will and Grace end up with the funnier half. Jack and Karen manage to make their own fun, with Jack trying to teach Karen to cook and finding himself one-upped by Will’s boss/Grace’s boyfriend Ben (Gregory Hines). If nothing else, this subplot gives viewers a chance to watch Gregory Hines deliver a little soft-shoe while Mullally can barely stay in character, she’s so charmed by him. Will and Grace are busy on a road trip to visit an old college professor (Orson Bean) who turns out to be a bitter old queen caught in a Who’s Gay-fraid Of Gay-ginia Woolf relationship with his best friend, played by Piper Laurie. It’s a chilling (and fairly hilarious) glimpse into Will and Grace’s worst-case scenario future, and yet another dead-on look at a deceptively complicated sitcom relationship.

“Brothers, A Love Story” (season three, episode 14): A pre-Grey’s Anatomy Patrick Dempsey shows up as Will’s sports-reporter boyfriend, who, to Will’s great dismay, is closeted at work. As standard sitcom relationship-obstacles go, it’s a relatively pertinent one (particularly in 2001), and it comments on Will’s tendency to allow himself to be, if not closeted, at least plausibly deniable. This time it’s Grace, and not Jack, acting as Will’s conscience, urging him to stand up for himself and not accept this closet-like treatment (Dempsey introduces Will as his brother). The whole episode builds to an all-characters convergence at a crab shack that is sub-Seinfeldian in its execution (Karen’s entire plot is a thin excuse to get her to the right place at the right time), but quite satisfying comedy-wise.


“Moveable Feast” (season four, episode nine): This hour-long episode might be the series’ best. It’s a triumph of construction, keeping all four characters together, yet giving time to each one of their storyline concerns, as they make a pact to do quick pop-ins at each of their respective family Thanksgivings. The show is always at its strongest when all four characters are together, bouncing off of one another, and the introduction of a cavalcade of guest stars—Debbie Reynolds! Beau Bridges! Nick Offerman! Lainie Kazan! Blythe Danner making her debut as Will’s mom!—gives the four leads plenty else to bounce off of. The uniting theme is that none of them feel as understood by their families as they do by their friends. (Well, not so much Karen, who’s been given a free pass by her jailbird husband, Stan, but hardly any of the unifying themes ever apply to Karen anyway.) And any episode that can combine four separate strands of honest character beats with Bobbi Adler’s “toldja so!” dance is a winner.

“A Chorus Lie” (season four, episode 15): For as much as Will & Grace garnered a well-earned reputation for overdosing on high-profile guest stars, its best deployment of such might well have been the highest-profile guest of them all. Matt Damon shows up as Owen, a shining star in Jack’s gay-men’s chorus group, until jealous Jack discovers his terrible secret: He’s straight! Not that necking with Grace on a couch would completely rule out his homosexuality, but he’s certainly hotter for Grace’s “rockin’ ass” than Will ever was in their college days. Damon is magnificently game for this show’s brand of broad comedy and bitchy one-liners, and putting Jack and Grace into the same subplot was a sadly underused tactic. Will and Karen don’t do too bad themselves, as he accompanies her to an event, where Karen has to live down the humiliation of Stan’s imprisonment. Will manages to overcome his usual revulsion to Karen and ends up helping her shove it in the face of her chief rival, Beverley Leslie (Leslie Jordan).


“Strangers With Candice” (season six, episode nine): The end of season four is a handy line of demarcation for anyone wondering when the show “went bad.” Just look for Harry Connick Jr.’s first appearance as Leo to mark the time. Leo was not one of the show’s better characters by a long shot (Connick never once delivered a line that was believable and always seemed to be laughing that he was on a show like this in the first place), but the downturn the show took was probably not entirely his fault. Leo was a symptom of a show that increasingly cared about only four things: Grace’s love life, Grace’s uterus, guest stars, and getting Jack and Karen to do and say increasingly insane things. This is all to say that there’s a reason why this list only includes two episodes from the show’s four final seasons. The very best example of the kind of episode this era produced is not accidentally one where all four main characters head out to dinner. There, they do pair off, with Will and Grace coping with their current romantic woes by flirting with random restaurant patrons (Tom Everett Scott for Grace, Kali Rocha for Will), no matter how bad an idea those flirtations are. The real highlight here is Karen and Jack engaging in one of their wackier subplots, as Karen ropes Jack into a prank war with her arch-nemesis, Candice Bergen. No matter how dire Will and Grace’s dating plots got in this era, Karen and Jack were almost always good for enough laughs to keep things going, and the Candice Bergen pranks were top-notch.

“Bathroom Humor” (season eight, episode 11): In the show’s final season, almost as if it was looking to give TV critics multiple excuses for “Will & Grace has run out of gas” stories, the show aired two live episodes. Both were rather hit-and-miss affairs, but this second attempt sums up the final-season episodes nicely. It’s essentially a one-room play in Karen’s bathroom, as Will, Grace, and Jack fight among themselves over their status as uninvited guests. Viewers get a random celebrity cameo (Matt Lauer, why not?), a lot of material that tries to be screwball, but just ends up shrill, and one or two bits that are just funny enough to save the episode from total disaster. (The episode takes advantage of the live-show gimmick by piling on the slapstick, and there’s a gag about pill bottles in Karen’s medicine cabinet that kills.) It’s worth watching for those delighted by Debra Messing and Hayes clearly having a ball trying not to laugh, but even more worth watching to see the condition of the show as it limped across the finish line.


And if you like those, here are 10 more: “To Serve And Disinfect” (season two, episode six); “Tea And A Total Lack of Sympathy” (season two, episode 10); “My Best Friend’s Tush” (season two; episode 22); “Gypsies, Tramps, And Weed” (season three, episode seven); “Coffee And Commitment” (season three, episode 10); “Past And Presents” (season four, episode two); “Crouching Father, Hidden Husband” (season four, episode three); “Stakin’ Care of Business” (season four, episode 10); “Last Ex To Brooklyn” (season six, episode two); “Flip-Flop: Part 1” (season six, episode 15).

Availability: All eight seasons are available on DVD.

Up next: Stephen Bowie digs into the 10 most representative episodes of the long career of writer, producer, and creator David E. Kelley.


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