Jennifer Lopez’s $20 Million Gamble: Why the Superstar Spent Her Own Money and Defied Skeptics to Tell Her Ben Affleck Love Story

A few months after Jennifer Lopez and Ben Affleck were married in 2022, Lopez got a call from Jane Fonda. The two had been friends since 2005’s “Monster-in-Law,” and it was Fonda who had introduced J. Lo when she received her star on the Hollywood Walk of Fame. Fonda was reaching out because Lopez had asked her to appear in a yet-undefined film (with music) that would examine Lopez’s romantic failures in some kind of meta way. Lopez wanted Fonda to play a member of her Zodiac love council. (More on that later.)  

Fonda had her doubts. So before deciding, she talked to Benny Medina, Lopez’s longtime manager, expressing skepticism about any project that seemed to excessively celebrate the Affleck-Lopez reunification. Medina relayed to Lopez Fonda’s thoughts: “I believe that everyone in the entire world is pulling for this relationship and this love. And the idea of how you present that is so sacrosanct, so important. It should be handled in a way that you aren’t overly flaunting it, so much so that it creates any form of criticism or resentment.” 

Lopez and Fonda then talked directly, in a conversation that is included in Lopez’s new documentary, “The Greatest Love Story Never Told,” one component of a self-financed $20 million three-part multimedia project examining Lopez’s life as a serial romantic. “I want you to know that I don’t entirely know why, but I feel invested in you and Ben, and I really want this to work,” Fonda says in the documentary, speaking for much of the universe. “However, this is my concern. Like, it feels too much like you’re trying to prove something instead of just living it. You know, every other photograph is the two of you kissing and the two of you hugging.”  

On screen, Lopez laughs. “That’s just us living our life,” she says. 

Fonda eventually agreed to be in the musical film. In the doc, Fonda expresses another universal worry. It was shortly after photos emerged of Affleck looking bored or cranky with Lopez at the Grammys in March 2023. “I got real scared, you know, with all that shit about the Grammys and he looks unhappy and I’m like, ‘Oh, my God, what’s happening?’”

Lopez reassures her. “Nothing! He was like, ‘I’ve become the symbol of the beleaguered man.’” 

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Not a ton of us like to dwell on our worst moments, but Lopez is different. Twenty years ago, “Bennifer” was a cute bunny that turned out to be a tasty snack for the tabloids. Lopez and Affleck met, they fell in love, they made Martin Brest’s classic “Gigli” and were hounded by the press, splitting up three days before their 2003 wedding.  

“Our relationship crumbled under the weight of the pressure,” Lopez tells me. “We lost a sense of ourselves, and we needed to separate because we didn’t know how to survive it. I had to figure myself out, and he had to figure himself out.” 

That was two decades ago. The media world has changed. J. Lo has earned more than $1 billion in box office receipts, and that’s just for her rom-coms. She now has a newsletter, 17.5 million TikTok watchers and a quarter-billion Instagram followers. She is now the cobra, and the tabloids are the bunnies. 

 

The first time Lopez was in love with Affleck, the crush of cameras took him away from her, leading her into multiple baffling relationships. This time, Lopez is turning the tables and seems intent on sharing every shred of their love while Affleck grudgingly follows along. (In the documentary, Affleck says, “Things that are private I always felt are sacred and special because, in part, they’re private.” He then delivers an understatement: “So this was something of an adjustment for me.”) 

Still, even a cobra is vulnerable. I ask Lopez if Affleck and other loved ones had told her that this project was, well, insane. 

“Everybody thought I was crazy,” she says with a loud laugh. “And by the way, I thought I was crazy.” 

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I didn’t know the scope of Lopez’s aspirations when I started this story. Last summer, I made my way to the Lopez and Affleck manor somewhere off Mulholland Drive for an oft rescheduled promotional chat about her new album, “This Is Me … Now,” a sequel to her 2002 album “This Is Me … Then.”   

The couple’s residence has multiple gates, much like a military installation. A security guy insisted I sign a nondisclosure agreement before I entered the property, which seemed strange since I was there to interview Lopez about her new record. There was an empty police car outside the main gate, but no matter — I was directed to another gate about a mile away, near the satellite parking for the dozen or so SUVs belonging to contractors and other employees. Eventually, I was taken by golf cart to what seemed like an annex to the main house. 

After a wait, Lopez arrived in a crème-colored pantsuit exposing just a touch of her famous age-defying midriff. She exuded wit, class and a rigorous skin regimen. We talked about her new record and how it explicitly addresses her restarted relationship with Affleck, just like the “This Is Me … Then” album addressed their earlier romance. (The first has a song called “Dear Ben,” the second a song called “Dear Ben Pt. II”) The new album is old-school Lopez, partly inspired by her teenage twins, whom she shares with her ex-husband, Marc Anthony. She’d been prepping for a private show and had “This Is Me … Then” playing in the house. She noticed her kids listening intently.  

“They said, ‘Is this you, Mommy?’” Lopez says with a smile. “I’m like, ‘Yeah, this is an album I did 18 years ago.’ I played them another song and asked them if they liked it, and they said yes, and I said, ‘I wrote this.’ And then they’re like, ‘Yeah, we like this more than the music you make now.’” Lopez laughs. “Ouch. But a good ouch.” 

Lopez is patient in answering my questions, but her responses are guarded. This seems odd since the record is pure first-person journalism about her love for Affleck, down to a song about the couple’s trip to Las Vegas to get married. 

Finally, after asking for assurances that I won’t repeat any of what she says until after rollouts, single releases and premieres, she tells me about the big three-part multimedia project I mentioned above. She says that the record “This Is Me … Now” is just the first part of that three-pronged attack on the world’s senses. There will also be an hourlong Amazon original musical film called “This Is Me … Now: A Love Story” and then a documentary about the making of the record and the film. (The film debuts on Feb. 16, the record drops the same day and the documentary follows on Feb. 27.) 

Someone then brings Lopez a laptop, and she says that what she’s about to show me will be embargoed until just before the project’s release. It’s a cut of “This Is Me … Now: A Love Story.” She pushes play. 

I don’t want to spoil things for you. But joining Fonda and Trevor Noah in a partly animated musical journey through many of the songs on “This Is Me … Now” are Post Malone, Sofia Vergara, Neil deGrasse Tyson, Keke Palmer and a few other famous randos. They’re all on that Zodiac love council examining Lopez’s romantic foibles. There is a special appearance by guru to the stars Sadhguru, which, according to the documentary, added $200,000 to the film’s budget. Affleck plays a wizened TV commentator.  

If this all sounds more than a little nuts to you, you’re not alone. Her inner circle had been telling her from the start that the project might be a really bad idea. After all, Lopez has been experiencing a career renaissance. She sang at the Biden inauguration, and at the 2020 Super Bowl, where she was famously forced to share the show with Shakira. Just last year, she had top streaming movies on both Netflix and Amazon Prime with “The Mother” and “Shotgun Wedding.” And, oh yeah, she also married Affleck in July 2022 after he proposed to her in her favorite spot: a bubble bath. 

But the world was not enough.  

Lopez began telling Medina untold stories about her search for love in the years between her first time with Affleck and the triumph of their reunification. Medina urged her to consider making an album about their reunion. “Let me put you in touch with some writers who can help you transcribe this,” Medina told her.  

Lopez then invited musicians over to the house, and, for inspiration, showed them a stash of letters Affleck had written her, which he’d titled “The Greatest Love Story Never Told.” In the documentary, Affleck comes into the room and seems taken aback when he sees his letters being bandied about. He says to the camera, “I did really find the beauty and the poetry and the irony in the fact that it’s the greatest love story never told. If you’re making a record about it, that seems kind of like telling it.” 

Lopez recorded the album in a converted home theater. At night, she’d play demo tracks for her husband.  

Soon she was talking about a “musical film” (Medina adamantly objects to anyone calling it a music video) and a documentary that would explore her lifelong journey toward love. Nobody quite got it.  

So Lopez called her longtime producing partner, Elaine Goldsmith-Thomas, in the middle of the night, telling her that she was kicking in $20 million of her own money to the project. (After it was completed, Amazon bought it for an undisclosed amount.) A potential partner had pulled out, she’d said, because they didn’t understand the thing. 

“I’m in New York,” Goldsmith-Thomas tells me, “and she’s saying, ‘I think I’m going to finance this myself.’ I was like, ‘Wait, what?’ I don’t even know what it is. What are you doing?’ I was worried. ‘Why are you sharing your story? It’s too personal. Stop it.’ It made me uncomfortable for her.”  

It was uncomfortable for others too. Khloé Kardashian was among many Hollywood types who declined to appear in the film despite Lopez’s requests. The irony that an icon from the most photographed family didn’t want to appear in her film was not lost on Lopez, who looks downcast in the documentary. “People are scared to put themselves out there,” she says on camera. “I get it. It took me a long time. I’m scared. But I don’t act like I’m scared — that’s the secret to my whole fucking career.” 

I ask Goldsmith-Thomas if eventually she became comfortable with the project’s direction. She responds succinctly. “No! She never won me over. I was petrified the whole time.”  

Goldsmith-Thomas remains nervous about the project’s release, but now understands why Lopez needed to do it. “I was afraid that she was telling her journey and that it would look like it was saying, ‘Here’s my journey from Ben to Ben.’ And it’s not about that. It’s about ‘Here’s what I’ve been through for the past 20 years, and I kept walking into the same wall and blaming the wall until I started to look at myself.’” 

This much is true: When the J. Lo biopic is made, there will be scenes from the Bronx, “Selena,” “Out of Sight,” “Jenny From the Block,” the eleventeen rom-coms, the marriages, “Hustlers,” singing at the Super Bowl and Biden’s inauguration. Then, and only then, there will be a whole hour on the “This Is Me … Now” multimedia project. 

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I talk with Lopez a second time — a couple of weeks ago, after she returns from making a guest appearance on “Saturday Night Live,” where she valiantly soldiered on after losing part of her weave on live television. She looks tired but happy, her eyes watering from a recent surgery to improve her vision. Lopez is talking about romance again, and the film. 

“I’ve been on this journey, and I’ve been trying to figure it out,” she says about her chronic quest for enduring love. ”Now I feel like because Ben and I have rediscovered each other — and now that we’re married — I have something to offer. This is the defining piece of work that’s going to close that chapter so I can move on to the next part of my life.”  

Do I believe Jennifer Lynn Affleck, née Lopez, will move on from writing/singing/dream journaling about love? I do not. This would be like Donald Trump existing without telling stories where an anonymous American general is always proclaiming him the bravest man in the world. It can’t be done. It is Lopez’s performances in both screen and real-life rom-coms that have kept the 54-year-old current when many of her peers have long been sentenced to philanthropic work.  

Her musical film is a literal catalog of love misadventures, resplendent with tales of ex-husbands, Puff Daddy-like characters and boy toys. On “SNL,” she sang her album’s title track in a dress made of rose petals. It includes this verse: “When I was a girl they asked me what I’d be / A woman in love is what I grew up wanting to be / It’s my melody / The symphony I seek.” 

This is who she is now, then and forever more. Her endless love jones is crucial to an image that allowed her to convincingly play, at 50, grifter-stripper Ramona Vega in “Hustlers.”  

Of course, there are risks involved in exhaustively showing your ass across the platforms. Within hours of the film going live, there will certainly be someone from Brockton, Mass., posting on social media that the “Jennifer Lopez Love Exploration Experience” is a calculated ruse — a carefully orchestrated three-card monte that will end badly for Affleck when Lopez reinvents herself yet again in 2029 with “Jen: This Is Sixty and Single.” But cynical takes on Lopez’s motivations have dogged the entirety of her career.  

It’s fair to ask if that has less to do with J. Lo and more to do with America fumbling to get comfortable with a let’s-get-loud Latina who is powerful enough to taunt Trump’s border policies by incorporating children in cages into her 2020 Super Bowl performance. There were pay disparities in Lopez’s early movie career that can only be attributed to Hollywood pashas believing a brown woman could not bring in big box office. And that kind of bias leaked into her first go-round with Affleck: The actor had recently dated golden girl Gwyneth Paltrow and began getting cozy with Lopez while filming “Gigli.” Not everyone in 2003 America appreciated that, and the two took a lot of shit — some deserved, much not.  

Lopez’s 2002 “Jenny From the Block” video is an iconic moment in her career, but she now says it was a mistake. According to Lopez, the idea to do a meta tabloid-themed video examining the Bennifer phenomenon was director Francis Lawrence’s idea, not hers. The video features shots of topless models on yachts, faux secret-camera footage and Affleck literally kissing Lopez on the ass while luxuriating on a yacht. The couple was roasted in certain corners like a rotating apple-mouthed pig at a family reunion.  

“‘Jenny From the Block’ should have been me back in the Bronx kind of walking around the neighborhood,” says Lopez. “That’s what that video should have been.” Lawrence, she says, convinced her to ask Affleck to be in the video. “We were so ourselves,” she says. “And we never thought that people would take offense or be angry at us for kind of living out loud and making a cool video. We were so naive.”  

But then, a moment later, she reverses field on “Jenny From the Block.” 

“I don’t regret it,” she says. “Even though it wound up turning out ugly for us in the media, it was very defining for me in my musical trajectory. Some very beautiful, iconic images came out of that video. It’s the one thing, no matter where I go people still go, ‘Hey, there’s Jenny from the block.’” 

There were moments when the media’s fun with Lopez’s addiction to love overwhelmed praise for her actual work. 2022’s “Halftime,” Lopez’s last documentary, concentrates on the year leading up to her performing at the Super Bowl, but it also captures the moment that her performance in “Hustlers” was getting awards hype. In the film, Lopez gets teary-eyed when she hears that a writer has declared her to be a “criminally underrated performer.” Then that moment of triumph is gone, and we see Goldsmith-Thomas and Medina looking devastated when Lopez doesn’t win a Golden Globe for the role and isn’t nominated for an Oscar. 

Minimizing Lopez’s accomplishments awkwardly resurfaced when she was in New York for “Saturday Night Live.” Someone dug up a quote from 2020 that host Ayo Edebiri had uttered on a podcast about Lopez: “I appreciate a good scam,” said Edebiri. “Today, I was actually thinking about one of my favorite scams of all time, because J. Lo is performing at the Super Bowl halftime show.” The quote was mentioned on air that night. Lopez did her best to shake it off. 

“She was mortified and very sweet,” says Lopez about talking to Edebiri backstage afterward. ”She came to my dressing room and apologized with tears in her eyes, saying how terrible it was that she had said those things. She felt really badly and loved my performance because we had just done my soundcheck and she actually got to hear me perform. She was just like, ‘I’m so fucking sorry, it was so awful of me.’” Lopez shrugs. “It’s funny. I’ve heard similar things said about me throughout my career, so it really didn’t affect me.”  

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Lopez’s forgiving nature can at least partially be attributed to having a partner who has also suffered the slings and arrows of outrageous fortune. An added plus? That Ben Affleck is an auteur who could help Lopez navigate the molasses swamp that is making a film with your own money. During the shoot, he watched from a close distance, and sometimes shot interviews with her, including one where he asks her if she’s ever really forgiven him for his actions in 2003. (Answer: Watch the film.) Sometimes he has a befuddled look on his face, perhaps because “This Is Me … Now: A Love Story” doesn’t exactly mesh with the straightforward storytelling style that won him the best picture Oscar for “Argo.” 

“He realized this was a surrealistic, fantastical journey that we were making,” Lopez says. 

Affleck told her to keep the film “really tight,” knowing that every penny was coming out of his wife’s pocket. He offered her a few simple filmmaking truths. He explained to Lopez how it all was going to go down. “Ben told me, ‘You’re gonna write it, and then you’re going to film it,’” remembers Lopez with a smile. “When you’re done, you’re going to do a rough cut, and you’re gonna see what it needs, and you’re gonna do three days of reshoots.’ That’s when I said, ‘I can’t do that — I don’t have any more money!’ But he was like, ‘You’re going to do a few days of reshoots, and then you’re going to go back in and edit it. And you’re going to tell your story.’” 

Lopez showed Affleck the final cut last year. 

“He said, ‘You made a movie. For you. You made a great movie. You did it.’” Lopez’s eyes mist up. “Honestly, I don’t care what happens now. That is the biggest kind of compliment that I could get.” 

Watching the documentary, it’s clear the whole creative process for Lopez was a stress bomb. One of her relationships in the musical film ends in violence as a man brings a glass house down on her. (It was filmed using green screen.) Is he meant to represent a specific partner? Lopez won’t say, only allowing that it was true to her journey. 

“The idea of the glass house was about how we get into these toxic relationships,” she says. “You have trauma from your past. You have these patterns you haven’t figured out yet. And you get into these relationships where you compromise yourself in ways that you never thought you would. Or you allow people to treat you in ways that you never thought you would.” She pauses for a second. “And that certainly has happened to me.”  

Today is the momentary calm before the hurricane of public opinion. I mention to Lopez that people are likely to be split on the “This Is Me …  Now” project — some will love it, some will hate it, some will see it as honest, and others will see it as a narcissistic cringefest.  

“I think when you put out any project, you get to a point in your life where you’re not doing it for every single person in the world to have the most beautiful opinion of it,” she says. “But I do think this is a beautiful project. The message is strong and the message is true. I think it’s a true piece of art, and I’m very proud of it.” 

We close with my expressing some skepticism that this is going to be the final chapter of the J. Lo love chronicles. Romance has been her jam for so long. She tells me it’s different this time. 

“It’s funny,” she says. “It’s like, ‘OK, so now I’m in a healthier, more loving, good relationship. I’ve gotten to this place where I feel more whole, to be more present in a relationship. But what is that like? I get to live that, and that’s even more challenging than the last 20 years.” 

Before saying goodbye, Lopez wants to clarify that one thing has not changed. “Don’t make a mistake,” she says. “I’m still going to be sexy.”

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Styling: Rob and Mariel/Forward Artists; Makeup: Ash Kholm/The Wall Group; Hair: Jesus Guerreo/The Wall Group; Manicure: Tom Bachik/A Frame Agency; Look 1(black dress) Dress: Grace Ling; Shoes: Dolce & Gabbana; Jewelry: Alexis Bittar; Look 2 (white dress) Dress: Blumarine; Look 3 (neon green dress) Dress: Georges Hobeika; Shoes: The Attico; Look 4 (green dress next to pool) Dress and shoes: Tom Ford; Jewelry: Bulgari