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HomeEntertainmentsFrom Gigli to Marry Me: A pop-culture timeline of Bennifer

From Gigli to Marry Me: A pop-culture timeline of Bennifer

From “He’ll Be Back” to him being back, plus “Jenny From the Block,” Gigli, and everything in between.

After winding its way through four presidencies, the rise and fall of Facebook, and a global pandemic, the two-decade saga of Bennifer has finally reached its climax (for now, at least), as Jennifer Lopez and Ben Affleck are engaged once again.

It’s a sequel that has improved on the original: the two seem better equipped to deal with the media scrutiny that impacted their relationship once before, and have no Gigli-sized millstone hanging around their necks this time. But since we’re all feeling a bit nostalgic about those long-ago days when Bennifer first captivated the nation, here’s a trip back through Ben and Jen’s relationship as marked by the pop culture they produced together (in one way or another) along the way.

“Jenny From the Block” music video (2002)

After making their relationship official in 2002, Lopez and Affleck first appeared on screen together in the music video for her single “Jenny from the Block,” which premiered on MTV’s TRL on Nov. 5 that year. The four-minute clip is centered around the theme of the media’s fascination with Bennifer, with numerous shots staged to suggest the paparazzi following and surveilling the couple at every turn. It’s enough to make Alfred Hitchcock blush. (Also, Affleck literally kisses Lopez’s ass after figuratively doing it with a full-page trade ad earlier that year, before they started dating.) Ironically, the video would only spur the frenzy around the couple to even greater heights.

While the song has since become her signature tune, it seems like everyone involved would prefer to forget the video. Affleck later remarked that he had misgivings about the clip: “If I have a big regret, it was doing the music video,” he said in 2008. “But that happened years ago. I’ve moved on.” Lopez, for her part, reportedly tried to get the video pulled from MTV after marrying Marc Anthony in 2004.

This Is Me… Then (2002)

Affleck is all over Lopez’s third studio album, released just weeks after the “Jenny” video in 2002. The singer even dedicated the record to him, with an inscription on the disc jacket (remember disc jackets?) reading, “You are my life… my sole inspiration for every lyric, every emotion, every bit of feeling on this record.” That much is apparent in songs like “Baby I Love U!,” “I’m Glad,” and, most obviously, “Dear Ben,” which begins with Lopez whispering, “You’re perfect.” Hold that thought.

Gigli (2003)

GIGLI, Jennifer Lopez, Ben Affleck, 2003, (c) Columbia/courtesy Everett Collection

Gigli holds an important place on the Bennifer-time continuum for two reasons. One, the first time Affleck and Lopez properly met was on the set of the movie in late 2001; and two, it quickly became the punchline for every single joke or snarky article about the couple after it was released in August 2003. The movie bombed hard, grossing $7.2 million worldwide on a $75.6 million budget and landing director Martin Brest (Midnight Run, Scent of a Woman) in movie jail until the end of time; critics were no kinder. Did its disastrous reception contribute to the couple calling off their engagement the next month? The world may never know.

Whether or not it deserves its reputation as one of the worst movies ever made, it’s clear that Gigli was primed to become the kind of turkey that the entertainment industrial complex eats up. As Affleck told EW last year, “Really what it taught me was how much everything around a movie dictates the way people see it. For being such a famous bomb and a disaster, very few people actually saw the movie.”

He added, “The studio at the time was intoxicated with the idea, because I had begun having this relationship with Jennifer Lopez, which was selling a lot of magazines and appeared to generate a lot of enthusiasm — they just predictably latched onto, ‘The [public] want a romantic comedy, they want the two of them together. They want to see that. More of it!’ And it was just, it was like that SNL sketch. Bad idea.”

Jersey Girl (2004)

Jersey Girl Jennifer Lopez and Ben Affleck

So all-consuming is Gigli‘s radioactive reputation that you may have forgotten Bennifer actually made another movie together. Starring Affleck as a single father whose first wife (Lopez) dies giving birth to their daughter, Jersey Girl had the misfortune of arriving in theaters just over six months after Gigli — and two months after Affleck and Lopez called it quits. Smith was put in the unenviable position of managing the fallout: “When they didn’t get married, I thought, I can’t leave in a shot of these two getting married,” he told EW of the couple’s characters. “I didn’t want to risk the chuckle factor. It would be a distraction so that when she dies 5, 10 minutes later, you’re not going to have the emotional impact.” Still, it didn’t help much: Jersey Girl earned a shrug from critics and proved to be another bomb, making only $35 million worldwide.

“He’ll Be Back” (2005)

Every breakup has its breakup song; J.Lo just made her own. Her first album post-Bennifer split, the unsubtly titled Rebirth, featured the even less subtle track “He’ll Be Back,” widely assumed to be about Affleck. (As if to quell any doubts, Lopez opens the song by singing, “I know better than anybody how it feels to want somebody so bad after you break up.”) It’s mainly notable now for its unintentional(?) prescience: “He’ll know he made a big mistake,” Lopez sings. “He’ll be back.”

“Marry Me” music video (2022)

And indeed, he would. Affleck and Lopez rekindled their romance in 2021, and two decades after “Jenny from the Block,” the actor appeared in another J.Lo music video — though he kept his face out of sight this time. While never officially confirmed, it’s widely assumed that Affleck can be seen cuddling Lopez in the video, released in March, for the eponymous ballad from her romantic comedy Marry Me. It proved to be another bit of clever(?) foreshadowing(??), as the couple finally announced their re-engagement the next month. What lies ahead for Bennifer? Well, we doubt they’ll be starring in another movie together anytime soon. But hey, at least it wasn’t Deep Water.

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