Mare of Easttown engrossed me. The White Lotus cast a morbidly fascinating spell. But my preferred pandemic binge may be Whitney Port’s reactions to old episodes of The Hills and The City.
The twin YouTube video series—Reacting to The Hills and Reacting to The City—are in some ways the opposite of the glossy MTV reality shows Port starred in between 2006 and 2010. There are no aerial shots of sun-drenched Hollywood or whizzing New York taxis; no sideswept bangs or drape-y going-out tops. It’s just Port (usually in sweats and scant makeup) and her husband, former City producer Tim Rosenman, alternately laughing and cringing on their couch in Los Angeles as they annotate the parade of bad aughties fashion (sagging beanies and wide belts, mainly) and massaged drama for hundreds of thousands of YouTube viewers. There is no Natasha Bedingfield belting “Unwritten” either: Without the rights to the The Hills’ adopted theme song, Port and Rosenman sing it themselves, often with a country twang.
Each episode of the YouTube series processing the original series is a digestible, slightly delirious snack. It is also an admirable exercise in self-awareness. While some of us wince at the sound of our own voicemails and can barely watch our awkward reflections in the Zoom grid, Port is valiantly replaying her 20s for our entertainment—from interning at Teen Vogue and launching her former fashion line, Whitney Eve, to dating ex–rocker boyfriend Jay Lyon. “I don’t know if it’s just because of my age that I felt older this year,” Port, now 36, tells me via videoconference from her tropical L.A. office, Rosenman at her side, “or if it’s because, watching these shows, I feel so old compared to my younger self.”
Port and Rosenman are generous in their reassessment of the reality juggernauts. She is more critical of herself than any of her castmates. (“Why am I being such a bitch already?” she muses of her long-ago sniping about costar Olivia Palermo on The City.) The tone of the YouTube shows is less a scene-by-scene analysis than a playful riff on the reality series’ absurdities, as illuminated by 15 years of hindsight. “This is already giving me the idiot shivers,” Port says in Reacting to The City, as she hears herself, in narrator mode, enthusing about a hip group of “downtown guys.” There are behind-the-scenes nuggets, too. In the first episode of The Hills, seeing herself and costar Lauren Conrad saunter into their first day as interns at Teen Vogue, Port notes matter-of-factly, “You can tell we did our own hair and makeup.” Rosenman brings the producer’s perspective: Of Conrad’s iconic (in the reality TV canon, anyway) mascara tear during a fight with roommate Audrina Patridge on The Hills, he groans, “Why’d they cut away from that? It’s all the way to her chin!”
Before the pandemic freed up the couple’s schedules, Port, a budding YouTuber who vlogs with Rosenman about their couple pet peeves and the travails of parenting their son, Sonny, did not rewatch reality TV, including her own shows. “I don’t go back and watch old Vanderpump episodes,” she says.
“No,” Rosenman says, “but I don’t know that Vanderpump has crossed over yet…”
Port interjects with a laugh: “To nostalgia.”
Von Dutch hats, pleated miniskirts, and even The Hills are back these days. (Port briefly appeared on Season 1 of the reboot, The Hills: The New Beginnings; Rosenman declined, not wanting to cede control of his image.) But now, thanks to Port and Rosenman, the source material has been resurrected too.
Port’s willingness to return to The Hills and The City is helped by the fact that, as she says, “I never really regretted anything that I did on those shows.” It’s an extremely rare statement from a reality alumna, but Port was always a voice of reason; a polished, one-woman Greek chorus offering sage advice to Conrad and actually being professional in professional settings. “You had a role,” Rosenman tells his wife. “Whitney was Lauren’s foil.” (Port demurs, saying that Conrad “always kind of knew the right thing to do.”) While Conrad, Heidi Montag, and company scandalized Hyde and Les Deux, Port was a gender studies major at USC, filming The Hills as a side job.
Before the couple’s (still ongoing) rewatch sessions, Port “had a little bit of imposter syndrome,” she admits. “So many amazing things happened to me at such a young age that I didn’t necessarily make happen…it always felt like right time, right place for me.” Looking back, though, “I’m able to see that…my work ethic and who I was allowed certain doors to open.”
Port never quite fit in, nor did she ever get “superclose” to her costars, including Conrad, who appears with her in a perfectly nice but not cuddly-close reunion video on Port’s YouTube channel. “I think the show hindered us getting as close as probably people thought that we were, because we had to keep a lot to being on camera and didn’t really develop much of a personal relationship outside of the show,” Port says of Conrad. “It’s a little bit foggy,” she adds with a wry smile, because Rosenman often lovingly teases Port for her fuzzy memories. “I just remember us…not necessarily clicking on the personal level that I think everybody thought that we did.”
Port and Rosenman walk a delicate line in addressing the nagging question of what was real and what was fake. Neither trashes the shows, but the issue comes up. “Watching back, I think I could have been a little bit more eloquent. I could have said more,” Port tells me, “but then again, I probably did, and they just edited.” When Conrad and Port appear to elevator-eye each other in The Hills premiere without introducing themselves, Port concedes on YouTube, “I think we said hi to each other but they cut it out.” But MTV casting Patridge at the pool in Conrad and Montag’s apartment complex? That really happened. When Port goes to dinner with Lyon on The City, Rosenman asks: “And this was real?” Port confirms that, yes, “we were really, like, starting to date each other.” It demands a certain level of security on Rosenman’s part to watch his wife date other guys, but there are adoring moments between the couple too. “You look amazing,” Rosenman remarks of a glamorous shot of Port in The City. Port: “This is when you fell in love with me, 100%.”
Indeed, The City ended in a love story; just not with anyone Port dated onscreen. Rosenman, a New York native, had watched Port on The Hills and crushed on her from afar. Previously a producer at VH1, he sought a job on The City when the spin-off came to New York. As a field producer who helped Port find an apartment and set up shoots at restaurants and clubs where she liked to go, he grew close to Port. “There were times during the show when I thought about quitting so I could really pursue her,” says Rosenman, “but the job was really important for me, and the show was important for Whitney”—then an aspiring designer wooed by the idea, she says, of a “beautiful look at fashion from a young girl’s perspective.” Rosenman says he risked getting fired if anything happened between them, so they both agreed to press pause on getting together.
At times, Rosenman’s feelings for Port made his job difficult: At one City shoot at Bergdorf Goodman, his boss pointed to Harry Fackelmayer, a man-about-town who would become a recurring character, and told Rosenman: “That guy’s good-looking. Go talk to him and get him to talk to Whitney,” Rosenman recalls. “I [didn’t] want to do that, but I had to do it.” Still, Port says that none of her onscreen love interests quite compared to Rosenman, whom she married in 2015. “I never ended up meeting anyone I liked that you had to be that concerned with,” she assures him, rather sweetly, in our Zoom interview.
The lack of onscreen fireworks—and Port’s aforementioned normalcy—didn’t necessarily serve her on The City, though, which was canceled in 2010 after two seasons. “You got kind of tired of watching someone making levelheaded decisions,” says Rosenman. “You want someone to be like, ‘Let’s go to Cabo and get drunk and hook up with someone’s boyfriend.’ Whitney wasn’t going to do that.” Port was disappointed when the show was canceled but ready to have her privacy back. “I never really loved being in front of the camera,” she says. “It wasn’t something that I fully felt natural doing.”
But—plot twist—it’s never felt as natural as it does now, on YouTube, in the mini reality show about her previous reality shows that she and Rosenman have created. On their couch in baggy T-shirts, playing drinking games pegged to show tropes—including Port’s habit of changing words ending in “ing” (laughing) into “ink” (laughink)—Port and Rosenman are relatable reality stars in their own right. “It’s really not until I started filming these videos with Timmy that I gained my comfort and I felt like I could really be myself,” says Port. “I feel like people have gotten to know me the most through these, not even through The City or The Hills.”
“You’re not a reality TV person,” Rosenman tells Port lovingly, “which almost makes you the most likable reality TV person.”