Pop culture obsessives writing for the pop culture obsessed.
Pop culture obsessives writing for the pop culture obsessed.
Law And Order: Special Victims Unit (Photo: Jason Green/Getty Images), The Sopranos (Photo: Getty Images), Freaks And Geeks (Photo: Chris Haston NBC/Getty Images) SpongeBob SquarePants (Screenshot: YouTube), The West Wing (Photo: Con Keyes/Los Angeles Times via Getty Images)

Dedication, animation, and Passions: 24 hours of 1999 TV

Law And Order: Special Victims Unit (Photo: Jason Green/Getty Images), The Sopranos (Photo: Getty Images), Freaks And Geeks (Photo: Chris Haston NBC/Getty Images) SpongeBob SquarePants (Screenshot: YouTube), The West Wing (Photo: Con Keyes/Los Angeles Times via Getty Images)
Graphic: Natalie Peeples
Illustration for article titled Dedication, animation, and Passions: 24 hours of 1999 TV

Though the Y2K bug turned out to be a dud, the TV of 1999 was anything but—there were good to great offerings in every medium, from animation to procedurals to sex-positive dramas. The debut of The Sopranos ushered in the era of the antihero (on the small screen, anyway), while The West Wing made doing the right thing look and sound snappier than ever. Futurama and Family Guy set off on their long and winding journeys, as both Freaks And Geeks and Roswell introduced us to some down-to-earth teens. A new set of New York detectives were on the case, a soap opera wreaked havoc, inspiring many a college student to get a late start to their day, while Batman and Garth Brooks reinvented themselves. Along with these exciting new offerings, 1999 also featured series-high moments for Buffy The Vampire Slayer, whose spin-off was launched in the same year. There were some momentous bows, as we bid farewell to Star Trek: Deep Space Nine and good riddance to Melrose Place; and a set of jeering silhouettes aboard The Satellite Of Love kept things from getting too saccharine. To help you truly appreciate the highs and occasional lows of end-of-the-millennium (we know, Toby Ziegler would disagree) TV, here are 24 consecutive hours of it, with the odd bonus clip, chance to grab a Cosmopolitan, and midday school break.

8 a.m.: SpongeBob Squarepants, “Help Wanted”

SpongeBob SquarePants didn’t quite emerge fully formed in 1999 as the paragon of absurd silliness that it would become later in its run, but a lot of groundwork is laid within the first minute of its first episode. The narrator introduces the city of Bikini Bottom, followed by a quick lampshading of the fact that SpongeBob lives in a pineapple (“Of course he lives in a pineapple, you silly!), and after that we see SpongeBob struggling to lift weights and greeting his meowing pet snail. It’s not immediately hilarious, but it’s certainly silly and it’s easy to see why it would be a hit with kids. The first hints of the show’s cleverness arrive later, when SpongeBob is making his way to the Krusty Krab to apply for a fry-cook job and Squidward runs in to warn Mr. Krabs not to hire him. That’s the smart twist in the show’s pilot: It knows how silly it is, allowing it to make jokes at the expense of its own silliness. That may seem like a lot of credit to give to a cartoon about a talking sponge, but that’s exactly why the show has been a hit for 20 years. [Sam Barsanti]

8:30 a.m.: Futurama, “Space Pilot 3000”

What could capture our collective mixture of fascination and unease with the rapidly approaching new millennium better than the opening moments of Matt Groening and David X. Cohen’s hearty welcome to the world of tomorrow, which sees dopey everyman Philip J. Fry sleep through the big New Years Eve 2000 celebration—and then the 999 other parties that followed. Even more than the show it kicked off, “Space Pilot 3000” leans heavily on a deliberately ambivalent “everything is high-tech and broken” sort of vibe, dumping Fry into a New New York where suicide booths are plentiful, crappy jobs are enforced by subdermal chips, and the cops have lightsabers—that still work just like nightsticks when they’re kicking the crap out of you for some petty (but very cool) crime. And yet, like so much of the high-concept mayhem that followed, it’s still a surprisingly sweet, emotionally satisfying show, drilling into its core elements: some friends, some jokes, and a guy who was born in the right place, but a very wrong time. [William Hughes]

Bonus clip: Futurama, “Love’s Labours Lost In Space”

Futurama was stocked with great recurring characters, including Zapp Brannigan, the wannabe Captain James Tiberius Kirk who had all the luck of a red shirt. We meet Zapp in the fourth episode of season one, which is the only time he comes close to impressing Leela.

9 a.m.: Batman Beyond, “Rebirth”

In 1999, the Batman that everyone had fallen in love with in Batman: The Animated Series and its The New Batman Adventures continuation did something that cartoon characters rarely do: He got old. Just as the original show was ending, Batman Beyond came along and jumped 20 years into the future to reveal what happens when Batman loses his faith in himself, with high-tech gangs running wild in a futuristic Gotham and no vigilantes left to fight for justice… at least until a teenager named Terry McGinnis (Will Friedle) crosses paths with an elderly Bruce Wayne (Kevin Conroy, reprising his role from The Animated Series). One family tragedy later, Terry has stolen a prototype bat suit that Bruce built before hanging up the cowl and is on his way to becoming a new Dark Knight. Batman Beyond would mostly try to distance itself from established Batman canon, preferring familiar parallels to direct tie-ins, but that only makes the few famous faces who turn up—police commissioner Barbara Gordon gets referenced in the pilot—that much more intriguing. [Sam Barsanti]

10 a.m. Downtown, “Sin Bin”

MTV’s animated slice of life Downtown was poised to be the ideal complement to Daria. Where the latter encapsulated living as an outsider in a nondescript suburb, the Chris Prynoski-created series put a surrealist spin on everyday teenage life in New York City. Downtown’s evergreen charm was largely powered by a cast of inexperienced voice actors and an animation style that elevated commonplace conversations to strangely captivating moments of art. Alex, Jen, Chaka, Mecca, Fruity, and Matt debated the best metro routes, swapped band class stories, and overestimated the merits of club life in ways that would seem mundane to someone on the outside. But what made Downtown stand above the rest was its ability to recognize the vitality of those everyday moments amongst friends. Despite its critical acclaim, Downtown only lasted for one season. Still, there is always this lingering hope that animated TV will take another chance on something so refreshingly familiar. [Shannon Miller]

10:30 a.m.: Home Movies, “The Art Of The Sucker Punch”

Loren Bouchard and Brendon Small’s deadpan classic only aired five episodes on UPN in 1999, robbing primetime viewers the chance to get in on early Brendon Small (the animated one, not the creator who voiced him) opuses like the Franz Kafka rock opera and the misadventures of Spiky McMarbles. Those episodes both look and sound like a work in progress, thanks to a pair of processes ported over from producer Tom Snyder’s flagship cartoon, Dr. Katz, Professional Therapist: The jittery Squigglevision animation process and the “retroscripting” method which left the dialogue for episodes like “The Art Of The Sucker Punch” largely improvised. (Further evidence that “Sucker Punch” is primordial Home Movies: The bad-influence soul of the show, H. Jon Benjamin’s Coach McGuirk, is barely in the episode.) Still, you can see the show Home Movies would become coming into focus as Brendon makes a perfectly cinematic stand against schoolyard bully Shannon (Emo Philips, finding the manipulative menace in his distinctive lilt), before finding out there might be more to this tough guy than any documentary’s camera could perceive. The show, like others featured here, eventually found the audience it deserved (and three more spectacular, non-squiggling seasons) on Adult Swim—but nowhere to the degree that Cartoon Network’s late-night block helped a ’99 premiere found later in this lineup. [Erik Adams]

11 a.m.: Friends, “The One Where Everybody Finds Out”

Midway through its 10-season run, Friends recharged itself by pulling off an unexpected romance between Chandler and Monica. After a surprise hookup in London at one of Ross’ weddings, the longtime friends realized that their particular brand of neuroses matched up extremely well: They weren’t perfect, but they were perfect together. While figuring out their fledgling relationship, the pair tried to keep it a secret. But everything came to a head in “The One Where Everybody Finds Out,” when after Phoebe spots the pair “fornicating” from Ugly Naked Guy’s apartment, she kicks off a web of deception designed to make Chandler and Monica come clean. Using her strongest asset—“my sexuality”—she attempts to seduce Chandler, so that he’ll have to admit he’s with Monica. This all leads to ever-elongating sentences that start out with “But they don’t know that we know that they know that we know” and one of the most awkward seduction scenes in TV history (Chandler: “I’m really looking forward to all the sex”). It’s a fittingly epic kickoff to the Chandler-and-Monica romance; after spending so much time on the Ross-and-Rachel roller coaster, viewers were just happy to see a Friends couple that finally focused on comedy instead of all the drama. [Gwen Ihnat]

11:30 a.m. (or whatever time you usually cut class to watch Passions)

By 1999, soaps were pretty par for the course. Even Passions—the final daytime drama to debut on network TV—had the typical bucolic community (Harmony), and the rich, powerful family (the Cranes) facing off against the salt-of-the-earth have-nots (the Lopez-Fitzgeralds). But Passions set itself apart from the very first episode, with on-location shots that left the studio, a rarity in the soap world, so that we actually saw Gwen Hotchkiss and Ethan Crane frolicking on the Harmony beach. But we also saw Grace Bennett experience strange visions of a ghostlike little girl, predicting Passions supernatural bent. In the second episode, we were introduced to Grace’s neighbor Tabitha (played by former Nanny And The Professor star Juliet Mills), a 300-year-old witch ready to wreak havoc on Harmony’s residents. We meet the assistant to aid her in this endeavor in episode five, when Tabitha’s child-size doll turns into a boy named Timmy, played by Josh Ryan Evans. Next to Marlena’s demonic possession on Days Of Our Lives (also written by Passions creator James E. Reilly), Timmy turning into a real-live boy was about the strangest thing ever seen on daytime television, and the captivating, wholly original pair of Timmy and Tabitha made Passions a hit. Sadly, Evans died due to a congenital heart defect on the same day that his own character’s death scene aired in 2002; the episode was dedicated to him. [Gwen Ihnat]

12:30 p.m. Freaks And Geeks, “Beers And Weirs”

It was only the second episode of Paul Feig and Judd Apatow’s soon-to-be cult phenomenon, but “Weirs And Beers” nailed everything people love about one of the most achingly funny (and painfully honest) depictions of high-school life seen on TV before or since. Lindsay Weir (Linda Cardellini), along with her new “freak” friends in high school, decides to throw a kegger when her parents go out of town. What ensues is the typical result of a bunch of unknown people swarming the teen house party—with the noteworthy twist that Lindsay’s little brother, Sam (John Francis Daley), and his geek friends have swapped out the real beer for non-alcoholic (much to the delight of the liquor store employee who sells it to them). The subsequent party features awkward unrequited crushes, party crashing from some way-too-old guys, and Lindsay’s former best friend Millie showing up to issue disapproving stares. The ’80s-set dramedy may have outdated cultural references (Jason Segel’s Nick spends the whole episode mourning the week-before death of Led Zeppelin’s John Bonham), but the emotional beats remain timely as ever, and the humor even more so. You’ll never hear the Doobie Brothers’ Christian groove “Jesus Is Just Alright” the same way again. [Alex McLevy]

1:30 p.m.: Star Trek: Deep Space Nine, “What You Leave Behind”

In the late ’90s, not even the venerable Star Trek franchise could hold out against the forces of serialization any longer. As the finale of not just the third live-action Star Trek series, but also a story arc that stretched back years, “What You Leave Behind” bears the scars of that struggle against episodic storytelling, for good and ill. The ill: The culmination of the series’ late-season fascination with poorly defined space demons and quasi-mystical ranting, ending with Ben Sisko plunging triumphantly-ish into some not-especially convincing flames. The good: Almost everything else, including the finale to the first storyline that ever really examined what happens when those good-hearted pacifists in the Federation are forced to go to war. Deep Space Nine went out as it lived—melancholy, and sometimes shockingly violent. There’s never been anything quite like it, either within its narrative universe, or without. [William Hughes]

3:30 p.m.: Mission Hill, “The Douchebag Aspect”

Aspiring cartoonist Andy French (Wallace Langham) leads the ideal life for a funky, 24-year-old urban bohemian circa 1999: undemanding day job, all the malt liquor he can drink, and a spacious loft in a hip neighborhood. There’s only one thing that could cramp this low-ambition fantasy, and that’s Andy’s dweeby brother, Kevin (Scott Meville), who moves to Mission Hill after mom and dad French ditch the suburbs for Wyoming—potentially teaching Andy something about responsibility along the way. In addition to capturing a strain of knowing, wiseass humor that straddles the fault line between the Spy slackers of the ’90s and the Vice hipsters of the ’00s, Bill Oakley and Josh Weinstein’s follow-up to their time as Simpsons showrunners is just a treat to look at. Future Wreck-It Ralph storyboard artist Lauren MacMullan’s character designs and color blocking make the pilot, “The Douchebag Aspect,” look like an alt-comic come to life. Mission Hill probably arrived too late for the in-crowd it celebrated and lovingly sent up—not that any of them even owned a TV—but at least its full, abbreviated run wound up on Adult Swim after The WB kicked the show to the curb. [Erik Adams]

4 p.m. Angel, “Rm W/A Vu”

Charisma Carpenter
Charisma Carpenter
Screenshot: Angel

The first truly great episode of Angel, naturally, focused on Cordelia Chase. (There was also some other stuff about Doyle and his way of life catching up to him. Angel was very good as the protective older brother. But really, this is all about Cordy.) Cordelia ultimately became the heart of the series, which—even if you loved the character—may have been ludicrous to think after her time on Buffy The Vampire Slayer, and “Rm W/A Vu” was the first episode to really showcase why, even before she received Doyle’s vision. In terms of Angel’s handful of first-season episodes that served as a reminder that “We’re not in Sunnydale anymore,” “Rm W/A Vu” is a necessary episode, with Cordelia having to contend with her past as “the nastiest girl in Sunnydale history” while also harnessing that fact to save the day from a vengeful spirit. (Because she’s really not a “sniveling, whiny, little cry-Buffy.”) Also, what’s more 1999 than Cordelia calling her eventual ghost roommate “Phantom Dennis”? (Okay, that would be Popular titling its pilot “The Phantom Menace” and second episode “Mo’ Menace, Mo’ Problems.”) [LaToya Ferguson]

5 p.m.: Now And Again, “Origins”

There were plenty of viewing options for sci-fi TV fans in 1999: The X-Files, Stargate SG-1, Farscape, Star Trek: Deep Space, Star Trek: Voyager. Some, like Farscape, played up the outlandish possibilities that came with a less grounded setting; others, like DS9, leaned into serialized storytelling. But they all tapped into recognizable, human (for lack of a better word) emotions, like paranoia, curiosity, and alienation. Now And Again, the sci-fi/adventure series from Moonlighting creator Glenn Gordon Caron, used its high-concept premise to explore the midlife crisis, which was usually the territory of family dramas and sitcoms (albeit played for laughs in the case of the latter). John Goodman appeared in the pilot as Michael Wiseman, an insurance executive with a happy home life who meets his precipitous end when he’s pushed in front of an oncoming train. A scientist (Dennis Haysbert) saves only Michael’s brain, which he promptly puts into the body of a gorgeous supersoldier (Eric Close). Instead of sending this hot new version of Michael home to his family (played by Margaret Colin and Heather Matarazzo), the scientist employs him as a secret agent. Caron made sure to keep things sexy with plenty of action sequences and shirtless scenes for Close, but the series was ultimately more interested in Michael’s struggle with his second chance at life. This exploration of life after 40 extended to Michael’s widow, Lisa (Colin), who launched a new career as a single parent. But neither the pathos nor the secret missions were enough to keep CBS’ interest, and Now And Again was canceled after just one season. [Danette Chavez]

6 p.m.: It’s after 5 p.m., which means it’s time for a cocktail and Sex And The City, “They Shoot Single People, Don’t They?”

By its second season, Sex And The City had become a huge hit by following the fun, fabulous lives of Sarah Jessica Parker’s Carrie and her three best friends, Samantha, Charlotte, and Miranda, as they traipsed around Manhattan. Their lives were a whirlwind of exclusive parties, designer outfits, and complicated relationships. So by episode four in season two, Carrie had broken up with Mr. Big, and her friends also happened to be single at the same time. Carrie is scheduled for a photo shoot proclaiming her as “Single And Fabulous,” but a late night before the shoot leaves her looking haggard, adding a question mark to that cover headline, and all the friends begin to reevaluate their own fabulous singleness. Carrie nearly hits rock-bottom as she heads out from a tartini party with a 24-year-old Bradley Cooper in his Porsche, and realizes in her ever-present voice-over that “if I went home with him, it would be the only time I’d ever slept with a man to validate my life.” So she gets out of the Porsche, and later heads to a café where she sits at a table for one and drinks a glass of wine alone. Sex And The City pushed a lot of relationships (hence the title), but episodes like this one underlined the adage that you can’t really be okay with someone else until you’re okay by yourself—although an impressive shoe collection and a supportive friend squad certainly helps. [Gwen Ihnat]

6:30 p.m. Roswell, “Pilot”

Let’s hearken back to the first supernatural era of The CW, one filled with witches, vampires, and other otherworldly beings. It looks a lot like the current Supernatural CW, filled with witches, vampires, and other otherworldly beings. Into that world came Roswell, Jason Katims’ adaptation of the Roswell High book series. What started off as a fairly compelling teen drama, fueled by the chemistry between leads Shiri Appleby and Jason Behr, became a wannabe X-Files, much to its own detriment—after the first season, the show (by network mandate) went the route of formulaic intergalactic adventures while veering wildly in tone. But when it was centered on star-crossed lovers Liz (Appleby) and Max (Behr) and their Roswell High pals and “Royal Four” clones, Roswell offered an enjoyable and often insightful look at the sense of alienation we frequently experience as adolescents. Along with existing series like Buffy The Vampire Slayer and the debuting Angel, the Roswell pilot helps make the case for 1999 being an exceptional year for teen movies and teen dramas. [Danette Chavez]

7:30 p.m.: Buffy The Vampire Slayer, “Graduation Day, Part 1 and 2”

For some fans, Buffy The Vampire Slayer would never again equal the highs of its high school years, as embodied in the two-part season-three finale. (They’re wrong, but we’ll let Amber Benson’s Tara Maclay point that out.) Still, Buffy (Sarah Michelle Gellar) and her Scooby gang’s senior year of high school was probably the show’s zenith in terms of pop cultural influence, as the story of a cheerleader-turned-vamp killer briefly became a part of the teen zeitgeist, and the critically beloved but always ratings-challenged WB staple seized hold of the moment with some of its most inspired storytelling. The season-long arc of our heroes fighting the mayor of Sunnydale (the excellent Harry Groener), along with the profound heel turn to evil of fellow Slayer Faith (Eliza Dushku), made for an enthralling conclusion, as Buffy’s fellow students rally to help the slayer they all secretly knew was operating right under their noses. Who wouldn’t want a graduation that culminates in your school exploding with an evil giant demon snake trapped inside? Her beau, Angel (David Boreanaz), may have departed after this season for his own series, but Buffy rarely shined as bright as this. (Another, less pleasant reminder of the era: The giant gap between the network airing part one and part two was the result of skittishness about the finale’s content after the Columbine High School massacre—back when that used to be a shockingly rare occurrence.) [Alex McLevy]

9:30 p.m.: The Sopranos, “College”

The Sopranos was in its earliest days when episode five arrived; nevertheless, “College” stands as a series high point (and won the show’s first of many Emmys for Outstanding Writing For A Drama Series). Until “College,” viewers saw Tony Soprano as a generally benevolent New Jersey family man, conflicted over his career in organized crime. Those two worlds collide in “College,” as Tony and his daughter Meadow go on a tour of university interviews. At a gas station in Maine, Tony spies a former made man who turned informant and entered witness protection, kicking off an intense cat-and-mouse chase. Meanwhile, Tony finally opens up to Meadow about his true career, and takes care of her after a night of tequila shooters. When we see this compassionate, affectionate father—this character we can’t help but like—brutally strangle his prey in broad daylight, we can’t help but be shocked. At the end of the episode, at Meadow’s hungover college interview, Tony waits outside while spying a telling Hawthorne quote in the hallway: “No man, for any considerable period, can wear one face to himself and another to the multitude, without finally getting bewildered as to which may be the true.” Tony’s double life, outlined perfectly in “College,” not only set up the series, but also it paved the way for the duplicitous TV antiheroes like Walter White and Don Draper that followed. [Gwen Ihnat]

10:30 p.m.: Law & Order: Special Victims Unit, “Payback”

Dick Wolf sought to justify the existence of his Law & Order spin-off, Special Victims Unit, by doubling down on everything: the urgency afforded by the ripped-from-the-headlines format, the interpersonal drama (which was treated with a much lighter hand for much of the flagship series’ run), delving into the lurid details of unspeakable acts. That was made clear from SVU’s intro, with its grave invocation of the “sexually based offenses” that are “considered especially heinous,” which is why we needed this group of “dedicated” detectives to neglect their personal lives and the civil liberties of others—and boy, did they ever. (The revelation that Linda Fairstein, the former New York prosecutor who helped railroad the now-Exonerated Five, consulted on the show in its inception further complicates the show’s legacy.) The series premiere, “Payback,” established how much more personal these stories would get, exploring the motivations of all parties, including the investigators. Over its 20 seasons (and counting), SVU has become increasingly invested in those detectives, revealing more of their home lives than is probably necessary. But that might also be what’s helped make the series the longest-running in the franchise, along with topicality and a great lead performance from SVU steward Mariska Hargitay. The success of SVU also made way for a few more spin-offs, including Law & Order: Criminal Intent and Law & Order: Trial By Jury. [Danette Chavez]

11:30 p.m. Third Watch, “Anywhere But Here”

Before Dick Wolf launched his “first-responder-verse,” John Wells expanded the medical drama of ER to include firefighters and police officers in the New York-set Third Watch. Wells, who’d previously looked at the intermingled lives of military professionals and civilians on China Beach, had bandied about the idea of a show centered around paramedics. He went to work on the new drama in 1999 with Ed Bernero, a former Chicago police officer, who wanted to draw from his time on the force. Bobby Cannavale rose to prominence in his first series regular role along with fellow ensemble members Kim Raver and Eddie Cibrian. The trio showed off their chemistry in “Anywhere But Here,” which was only the second episode of the series, but earned Third Watch a place among Wells’ most compelling productions. Another highlight came in 2001, via the series’ testament to the bravery of the first responders at Ground Zero. [Danette Chavez]

12:30 a.m.: Melrose Place, “Asses To Ashes”

By the time of its series finale, Melrose Place was hardly recognizable anymore. Characters who fans had first fallen for like Jake, Alison, and Sydney were long-gone, with Jane, Michael, and of course, Heather Locklear’s Amanda as the only remaining familiar faces from the show’s earliest days. Troublemakers like Peter (Jack Wagner) and Lexi (Jamie Luner) had joined the cast, and since then pretty much every character on the show had hooked up with, and sometimes married, everyone else. Campy to the last, Melrose Place closed out by wrapping up its psychotic cheerleader storyline, as noted showkiller Rena Sofer’s Eve tried to out-Kimberly Kimberly by kidnapping and trying to kill several Melrose Place residents. Even Michael has to wonder if it’s the apartment complex that inspires so much unhinged behavior, musing, I was pretty normal when I moved in here too—so was Kimberly, Sydney…” The show ends with Peter and Amanda faking their deaths to escape; naturally, Eve shows up in her cheerleader outfit at their funeral to toss Peter’s “ashes” at Lexi before getting carted off in handcuffs. But Peter and Amanda are going to live the rest of their days far away from Melrose Place, on a private island where Peter predicts they’ll have a bunch of kids and name them after Billy, Alison, and other MP residents—about as happy an ending as we could have hoped for from such a frequently twisted show. [Gwen Ihnat]

1:30 a.m.: Family Guy, “Death Has A Shadow”

It’s fitting that the first moments of Family Guy ever seen by America weren’t even of the Griffin family, the central characters around whom the series revolves. No, the opening scene is a satire of The Brady Bunch, in which kids Greg and Jan are punished with trips to the snake pit and chamber of fire, respectively—an apt way to introduce a show better known for its rapid-fire cutaway gags and pop culture references than for any emotionally meaningful sitcom stories. Peter, Lois, Chris, Meg, Stewie, and family dog Brian have taken on well-established identities over the course of the show’s 17-seasons-and-running lifetime, but they have always functioned more as joke-delivery systems than as real people, and the first episode reinforces that. For the short-attention-span theater consciousness that was developing in TV in 1999—primarily over at Adult Swim, where reruns of the series later made it enduringly popular (and brought the show back from cancellation)—Family Guy turned out to be the prescient Molotov cocktail of absurdist, whip-pan humor toward which interest was trending. (With a healthy dose of lazy, cheap-shot jokes, of course.) [Alex McLevy]

2 a.m.: Undressed, “The Odd Couple”

As you might have guessed from the title, MTV’s Undressed was a no-frills half-hour drama with sex on its mind: not just the act (though there was lots of that), but the pursuit of it and the psychology behind what was driving our pursuit of it. Undressed ran for six seasons and 222 episodes, yet was never properly claimed as a guilty pleasure, perhaps because the frank conversations about sex, relationships, and queerness, were too important to disown (which might also be why MTV plans to reboot the show). At first glance, the series from Roland Joffé (director of The Killing Fields, making an interesting pivot from feature films) was about as subtle as an old CK One ad, with exceedingly plaintive dialogue about who wanted to sleep with whom and why. But all the beautiful people of different races, ethnicities, and sexual identities—including future stars like Christina Hendricks, Pedro Pascal, Katie Aselton, and Nicholas Gonzalez—featured on the show were even more invested in making a personal connection in an increasingly tech-driven world, a theme found in other late-’90s artifacts like The Matrix and American Beauty. Sure, they were often having these frank conversations in their skivvies, but what’s more 1999 than that? [Danette Chavez]

2:30 a.m.: Mystery Science Theater 3000, “Show 1001: Soultaker

The Satellite Of Love’s final cable run began with a little blast from the past: Original test subject Joel Robinson (Joel Hodgson) and second second banana TV’s Frank (Frank Conniff) put in season-premiere cameos—a poignant full-circle moment for Hodgson, who parted from the franchise he created six years earlier. It’s the best kind of fan service, wrapped around a prime piece of supernatural ’80s cheese that Mike Nelson (Michael J. Nelson), Crow T. Robot (Bill Corbett), and Tom Servo (Kevin Murphy) make a total meal out of, an afterlife saga with a reincarnation twist starring the late Robert Z’Dar and Joe Estevez—though, as Crow points out, “Does anything really star Joe Estevez?” [Erik Adams]

4:30 a.m.: Farscape, “Premiere”

1999 was a watershed year for digital effects—something that The Jim Henson Company, creators of some of the most beloved practical effects work known to man, apparently took as a challenge. Hence Farscape, which dazzled with its alien puppet creatures, even as its talented crew was still finding its footing in the show’s opening trip around the sun. Said tale sees human astronaut John Crichton (Ben Browder) blasted out of a wormhole into the far-ass-end of the universe; trapped on a former prison ship of escaped alien fugitives, he receives roughly nine different forms of culture shock in rapid succession—including one initiated by his shipmates’ several foot-long tongue. Farscape would eventually mature into one of the most emotionally intelligent science-fiction shows ever to grace the genre—albeit one with an enduring interest in horniness and fart jokes— but in its opening salvo, the building blocks were already there: amazing puppets, quick-moving dialogue, and one lonely Earthman, stranded very far from home. [William Hughes]

5:30 a.m.: Saturday Night Live: Garth Brooks/Chris Gaines

Twenty years later, Garth Brooks’ intense method-acting experiment known as fictional Australian pop legend Chris Gaines is still one of the stranger blips in pop culture (which begot two charting singles, including the recently resurrected “Lost In You”). What should have resulted in a thoroughly researched film—The Lamb—devolved into a collection of honest efforts from Brooks to garner public interest. On November 13, Garth Brooks assumed hosting duties on SNL with Chris Gaines billed as the very special musical guest. It was a bizarre risk that Brooks, one of the biggest recording artists in the industry (and host of SNL the year prior), could ultimately afford to take. The appearance was also indicative of the adventurous spirit of entertainment during that time. At the cusp of a new millennium, 1999 was all about taking forward leaps and attempting feats that felt fresh. Had The Lamb come to fruition and been even mildly successful, Brooks’ effort would have likely been hailed as a sign of marketing brilliance. For now, it’s just an odd moment from a guy that dared to believe in something. [Shannon Miller]

7 a.m.: The West Wing, “In Excelsis Deo”

The West Wing already offered an almost idealized depiction of government when it debuted in 1999—not a bigotry-free utopia, of course, but a world in which our representatives occasionally fought back instead of constantly wringing their hands about civility. As President Josiah Bartlet, Martin Sheen combined the gravitas needed to lead with the compassion that inspired others to follow. (President Bartlet also managed to avoid ill-fitting suits and having crud around his nose, but those are cosmetic things.) The series has grown both more comforting and frustrating upon rewatch; it’s nice to think there’s a time we can pinpoint as being more progressive, but we’d need to ignore the fact that the fight for equality has been ongoing, and that the late ’90s were far from halcyon days. In addition to establishing a tradition for delivering wonderful Christmastime episodes, “In Excelsis Deo” touches on both of these conflicting perceptions—on the one hand, there are a couple of sweet B-stories involving Christmas shopping and President Bartlet’s penchant for rare books. But C.J. Cregg (Allison Janney) also struggles to get Leo McGarry (John Spencer) to consider anti-hate-crime legislation, while Toby Ziegler (Richard Schiff) reckons with the government’s indifference to veterans, a problem that even President Bartlet isn’t trying to solve single-handedly. It’s a great reminder that even on The West Wing, progress is hard won. [Danette Chavez]