How ‘Jenny From the Block’ Went From Jennifer Lopez’s Triumph to Ben Affleck’s Shame

Nearly 20 years after their breakup, Ben Affleck is still asked about his ex, Jennifer Lopez. This week, the Oscar-winner was on The Hollywood Reporter’s Awards Chatter podcast to look back at his career. And Lopez’s name came up:

“‘You know, there’s always a story of the month, and me dating Jennifer Lopez happened to be that tabloid story at the time when that business grew exponentially,’ Affleck reflects, though he shuts down any notion that he or she ever courted the attention. ‘Still, to this day, [some] will go, ‘I see you out there in the paparazzi and the pictures!’ It’s like, ‘Yes, I left my house and took out the trash. It’s not like I’m trying to—’ And it’s still like, ‘You were taking a pap walk!’ As if, if you leave your house, you’re only doing so in the hope that you could be so lucky that you could end up as the sixth item in The Daily Mail. It’s absurd!’

“He says of Lopez, with whom he split in January 2004 but remains friends: ‘People were so fucking mean about her — sexist, racist. Ugly, vicious shit was written about her in ways that if you wrote it now you would literally be fired for saying those things you said. Now it’s like, she’s lionized and respected for the work she did, where she came from, what she accomplished — as well she fucking should be! I would say you have a better shot, coming from the Bronx, of ending up as like [Justice Sonia] Sotomayor on the Supreme Court than you do of having Jennifer Lopez’s career and being who she is at 50 years old today.’”

As men often do when complimenting women, Affleck is trying to praise Lopez for her perseverance and the longevity of her career, but he does it in such a condescending way that it’s more cringe-y than commendable. The truth is, Affleck has always seemed a little awkward when discussing his former relationship with the Emmy- and Grammy-nominated multi-threat.

Of course, he was awkward back then, too. I couldn’t have been the only person this week who saw Affleck’s comments and immediately thought of “Jenny From the Block.” More specifically, I thought of the video. And even more specifically, I thought of Affleck in the video. “Jenny From the Block” was part of a string of hit singles for Lopez, the 2002 smash one of the centerpieces of an album devoted to her love for Affleck. But in popular culture, “Jenny From the Block” was simultaneously viewed as Affleck’s humiliation — an indication of how demeaning it was for him to be seen as some boy toy. I’m not sure Affleck has ever gotten over that.

Lopez has been world-famous for so long it can be easy to forget that, at one time in her life, she wasn’t. Born in the Bronx to Puerto Rican parents, she was singing and dancing at an early age. “My mom worked two jobs and my dad worked the night shift at Guardian Insurance,” she wrote in her 2014 memoir True Love. “My sisters, Leslie and Lynda, and I shared a bed, and every morning we were bundled up and sent off to Catholic school. That was why my parents worked all those long hours, so they could pay for a good education and raise us right.”

She seemingly could do anything: In school, she was a track star and, eventually, she established careers as a dancer, an actress and a singer. By the turn of the century, she’d had a blockbuster album (On the 6) and been the star of acclaimed films (Selena and Out of Sight). And her next project seemed incredibly promising, landing in her lap thanks to a bit of a luck: Halle Berry was supposed to co-star with Ben Affleck in a crime comedy called Gigli, but she had to drop out because of her commitments to the X-Men franchise. Berry’s loss was Lopez’s gain, with Variety reporting that she’d receive “a $12 million payday against a high single-digit percentage of the backend — a significant salary increase for the entertainer.” Affleck was riding high thanks to the super-cheesy (but very successful) Pearl Harbor, and the director, Martin Brest, had guided Al Pacino to his long-deserved Oscar for Scent of a Woman. Who wouldn’t have been excited for the film?

You probably know what happened next. But let’s delay that for a second and focus first on Lopez and Affleck falling in love, their relationship coinciding with the end of her second marriage, to director and choreographer Cris Judd. Before audiences saw a second of Gigli, they knew all about Bennifer’s whirlwind romance, leading to the announcement of their engagement in the fall of 2002. Around the same time, Lopez released her third record, This Is Me… Then, which was inspired by their courtship. “You are my life … my sole inspiration for every lyric, every emotion, every bit of feeling on this record,” she wrote in the album’s dedication.

Initially, part of the couple’s appeal to the media was how seemingly different they were. Not that Affleck saw it that way. “She was very much like the kind of girl I went to high school with,” Affleck told The Hollywood Reporter this week. “It was a very socioeconomically mixed, ethnically mixed place. Those differences that seemed to shock America were meaningless to me.”

“You know, he actually surprised me when we first started getting to know each other,” Lopez said in an MTV interview right before This Is Me’s release. “He would be singing the hip-hop songs. He loves Ja Rule, he loves Nelly, he loves Snoop. He would know all the lyrics to these songs. He’d just start singing, and I would be like, ‘What is that?’ And he’s like, ‘That’s Snoop from back in the day.’ I’d be like, ‘What?’”

Affleck’s influence on This Is Me could be felt in lovey-dovey songs like “Loving You,” “I’m Glad” and “Baby I Love U!” But Lopez also wanted to take a moment to look back on her life and reflect on where she’d come from. After years in the limelight, and now with the man with whom she imagined starting a family, she wanted to remind people that it hadn’t always been this way. “[Y]es, there’s a public image that I enjoy — I love dressing up. I love feeling glamorous. I love jewelry and beautiful things,” she wrote in True Love. “But I’m still that little girl who’s playing the part of a movie star, that same girl from the Bronx wearing big hoop earrings and listening to hip-hop.”

And so she wrote “Jenny From the Block.”

Years before Drake set the record straight on his pre-fame years with “Started From the Bottom,” Lopez did the same with “Jenny From the Block,” which was both a jubilant celebration of her success and a self-conscious rebuttal to anyone who thought she’d abandoned her roots. This Is Me’s first single felt like a mission statement, with Lopez declaring, “From In Living Color to movie scripts / To On the 6 to J. Lo to this / Headline clips / I stay grounded as the amounts roll in.” But even though she was buddies with Oprah, that hadn’t meant she’d changed. “Nothing phony, don’t hate on me,” she sings. “What you get is what you see.”

Riding a breezy, bouncy beat, “Jenny From the Block” wasn’t as assaultive as the luxury rap of Lopez’s peers, who aggressively lorded their wealth over the listener. Rather than seeming obnoxious, she was grateful, appreciating her career and her life and refusing to apologize for any of it. And audiences responded: The song peaked at No. 3 on the Billboard charts, helping to push This Is Me to double-platinum sales.

Then, of course, there was the video.

The conceit was simple: As a celebrity, Lopez had to deal with endless media attention, especially from the paparazzi. And so, much of the video was shot from the perspective of an imagined photographer’s telephoto lens trying to get a glimpse of the singer and her fabulous life. There’s also what’s meant to look like surveillance footage within the video, as if Lopez is a lab rat being constantly observed. The entire “Jenny From the Block” clip was her attempt to suggest the downside of success — you’re constantly pursued, your every action scrutinized.

“We try to make the best of it,” Lopez said in that same MTV interview about her and Affleck’s struggle to protect their privacy. “I’m not saying there’s not times that we wish [we] could just be going to the movies and come out and there’s not a crowd there waiting. You just want to spend your Sunday afternoon not working, but at the same time, we both love what we do. If that’s something that’s part of it, then that’s fine. We feel the love, and we’re very happy about it.”

But although “Jenny From the Block” was Lopez’s triumph, it soon proved embarrassing for Affleck. While Lopez is in the power position in the video, Affleck came across as little more than a kept man — a himbo dutifully applying sunscreen to his girl’s body or lounging around in a bathrobe. In the public’s mind, there was something demeaning — something unmanly — about a big movie star being reduced to serving as the plaything of a pop star. Of course, Lopez was more than that, but nonetheless the impression lingered. His career was supposed to be bigger than hers — why was he lowering himself in that way?

Even back then, Affleck suspected that something else was going on, telling Rolling Stone in 2004, after they’d split up, that the backlash to their pairing “had something to do with race and class. That pushed a button. This is a country that flew into a gigantic uproar about Janet Jackson’s breast. There’s still a heavy-duty puritan influence going on, and we still hold ourselves to a pretty chaste ideal, which includes, buried within it, the tradition of people being with people like them. We were thought of as two different kinds of people, not just racially but culturally.”

And while that might have been the case, I think the video sparked such a strong response for another reason. What was oddly prescient about the “Jenny From the Block” clip was how it both anticipated the rise in reality television and the public’s love/hate relationship with celebrity pairings. The Osbournes started that same year, with The Simple Life just around the corner, both of which helped to establish a beachhead for programs that let us inside the world of the rich and famous. (Keeping Up With the Kardashians and the Real Housewives franchise were still a few years off.) And while there had been supercouples before, Bennifer modernized the notion that we should consider two famous people dating as an indivisible entity, as if their relationship was its own living organism with specific personality traits and quirks. “Ben wanted to be — believe it or not — quiet and not be in the tabloids,” Lopez recalled in 2019. “And it was the beginning of the tabloid era, and we were kinda out there. I remember stacks of magazines, and we were on it every week. It was scary. It was overwhelming for both of us.”

Whether it was racism, class, sexism or the public’s exasperation with celebrity culture, Lopez and Affleck were turned into a punchline, a joke not helped by the sheer awfulness of Gigli, with reviewers annoyed with the film as much as they were with the whole Bennifer phenomenon. Interestingly, though, the movie (like the “Jenny From the Block” video) reversed traditional gender roles in some intriguing ways, letting Lopez’s lesbian mobster call the shots and ordering Affleck’s doltish hood to go down on her. (Gigli was endlessly mocked for Lopez’s “It’s turkey time … Gobble, gobble” reference to oral sex.) To be clear, the film isn’t good, but its willingness to play around with sexual mores ended up being a bad look for Affleck. Both in the video and the film, he just seemed like a hunky chump — emasculated and laid low. “I was actually in the very worst position you can be in in this business,” he told The Hollywood Reporter about that period of his life, “which is you can sell magazines but not movie tickets.”

Like a lot of Hollywood romances, Bennifer wasn’t meant to last. “Ben Affleck and I called off our wedding,” Lopez recalls in True Love, “ending our very public relationship in suitably dramatic fashion just days before we were to walk down the aisle of a fairy-tale wedding we had planned for months. It was just the cover of a magazine or a headline to everyone else — today’s joke, tomorrow’s trash — but for me, when Ben and I split up at the moment when I thought we were committing to each other forever, it was my first real heartbreak, it felt like my heart had been torn out of my chest.”

People tend to be pretty cynical about celebrity romances, as they tend to be cynical about celebrities in general. There’s always something a little too constructed about stars that keeps them from feeling like they have actual emotions. But I imagine that must make it even harder on them when they’re in a bad place — the whole world just assumes it can’t be that bad. (After all, they’re wealthy and famous and beautiful — tough life.)

Regardless, both Lopez and Affleck moved on. She has continued to be a multi-hyphenate — tellingly, her follow-up album after the breakup was titled Rebirth — and earned the best reviews of her acting career thanks to 2019’s Hustlers. Meanwhile, he did the thing that most male movie stars do to gain legitimacy. He took on more serious roles — he’s superb in 2006’s Hollywoodland — and pivoted to directing, earning a producing Oscar for his thriller Argo. He focused on being considered an artist, not someone who would go on and on about his girlfriend’s butt, and went from boy toy to respected Hollywood figure. It’s a good way to get over the embarrassment.

Of course, what’s funny is that, for a whole generation, the “Jenny From the Block” video is how they first became obsessed with Affleck as a sex symbol. They weren’t embarrassed for him — they were turned on. In fact, it’s fair to say that, for some people, Affleck isn’t a two-time Oscar-winner — he’s the love interest in a Jennifer Lopez video. For them, it’s the most significant artistic statement he’s ever made.

When Lopez performed at the Super Bowl halftime show last year, “Jenny From the Block” was her opening song, still triumphant and still an anthem. Although it came from an album that was about the two of them, “Jenny From the Block” was always her song — about her life and her vision of herself. In hindsight, it was only fitting that Affleck was merely an accessory in the video. Think of all the male singers who had their girlfriends pose as eye-candy in their clips — this time, it was the guy’s turn.

Watching it now, I’m struck by how the “Jenny From the Block” video is so much a warning about the fishbowl of stardom that was coming to envelop so many celebrities in the 21st century. For a lot of viewers, it probably seems pretty inviting. But the strangeness we feel when watching the clip is sensing Lopez and Affleck’s discomfort about the suffocating reality they were now in together. They don’t seem like two people in love — they look like they’re trapped. Lopez wrote the song to say that she hadn’t changed. Unfortunately, the video suggested that the whole world around her had.

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Tim Grierson

Tim Grierson is a contributing editor at MEL. He writes about film and pop culture for Screen International, Rolling Stone and Vulture.