Ain’t It Funny, Jennifer?

There was a moment in 2001 when Jennifer Lopez seemed almost impossibly complete. She had conquered cinema, moved into music, turned her name into the abbreviation J.Lo, become one of the most photographed women in the world and acquired that rare form of celebrity in which clothes, lovers, songs and even the movement of the body begin to belong to popular culture. Then came Ain’t It Funny, a Latin-pop song written with Cory Rooney, and with it a video by Herb Ritts in which Lopez appeared sun-burnished, dark-haired and almost mythological, wandering through a sepia landscape towards a fortune-teller, dancers and an irresistible stranger. The song had first been intended for The Wedding Planner, but director Adam Shankman decided its Latin character did not suit the film. It went instead onto her second album, J.Lo, and became one of the defining images of her early musical life.

In retrospect, the title seems almost mischievously suited to the woman who sang it. Ain’t it funny how often life gives a person precisely what she believes she wants, then changes the meaning of the gift? Lopez has spent much of her public life inside that question. She wanted love and found it repeatedly. She wanted marriage and married four times. She wanted permanence and discovered, more than once, how fragile permanence can be. She became one of the world's most recognisable embodiments of romantic confidence while living through relationships marked by jealousy, separation, reconciliation, engagement, divorce and return. There are quieter lives, certainly, but very few more public ones.

Jennifer Lynn Lopez was born in the Bronx in 1969 to Puerto Rican parents. Her father worked in computing and her mother was a teacher. The family was not wealthy, and Lopez grew up sharing a bedroom with her sisters in Castle Hill. Dance came early. So did the conviction that performance might provide a life larger than the one immediately before her. Long before the couture gowns and private jets, there were dance classes, auditions and the hard arithmetic of an ambitious young woman attempting to convert physical discipline into employment.

Her first great advantage was not beauty, although beauty undoubtedly mattered. It was movement. Lopez understood her body professionally before the world began discussing it commercially. Dance gave her command of posture, rhythm, gesture and the mysterious confidence with which some people enter a room already knowing where every eye will go. That quality never left her. Even when critics questioned the range of her singing voice, they rarely doubted the spectacle. She knew how to perform a song with the whole body, how to turn choreography into character, and how to make glamour appear physical rather than decorative.

The sex appeal arrived almost as a consequence. Lopez was voluptuous in an era when Hollywood was still heavily invested in another ideal, and she did not apologise for it. The famous green Versace dress at the 2000 Grammys became one of the great fashion images of its age, but the fascination was never really about fabric. It was about confidence. Lopez understood that sensuality could be theatrical without becoming vulgar, that a woman could command the room by appearing entirely at ease with being looked at.

That confidence made Ain’t It Funny an especially effective vehicle. The original song was Latin pop with salsa and disco inflections, written by Lopez and Cory Rooney. Herb Ritts, one of the great celebrity photographers and image-makers of the period, directed the video. Lopez appears travelling through a dusty, dreamlike world, encounters a fortune-teller, is absorbed into a community of women, dances in a flamenco-influenced sequence and meets a handsome stranger played by Eduardo Verástegui. The film is romantic fantasy rendered in ochre and sunlight, and Lopez is its unmistakable centre.

The song itself concerned the disappointment between imagined love and actual love, the strange way desire can survive even when the person desired proves unsuitable. This was not unusual pop material, but with Lopez it acquired an accidental biographical resonance. Her life, even then, was becoming an elaborate study in attraction and disappointment.

Her first marriage was to Ojani Noa, a Cuban waiter whom she married in 1997. It lasted roughly a year. She later reflected that marrying simply to avoid loneliness was no guarantee against loneliness. The relationship subsequently produced legal disputes concerning efforts by Noa to publish material about their marriage, an early warning of the price Lopez would repeatedly pay for having private relationships under public scrutiny.

Then came Sean Combs, the rapper and producer then known as Puff Daddy. Their relationship placed Lopez much nearer the centre of hip-hop celebrity. It was glamorous, volatile and heavily photographed. In December 1999 she was with Combs during the notorious nightclub shooting in Manhattan that injured three people. Lopez was detained and questioned but was not charged. Combs went to trial and was acquitted. Years later Lopez described the relationship itself as emotionally destructive and said she suspected him of infidelity, though she acknowledged she never caught him in the act.

After Combs came Cris Judd, a dancer she met through the video for Love Don’t Cost a Thing. They married in September 2001. The marriage soon collapsed. By July 2002 they had separated, and the divorce was final the following year. Lopez later spoke of Judd with affection, describing him as a good man while admitting that love alone had not been enough to make the marriage work.

And while that marriage was dissolving, Ben Affleck entered the picture. The two met while making Gigli, one of those films remembered less for artistic merit than for the catastrophe surrounding its reception. Yet from that failure emerged one of the most successful celebrity stories of the century. Lopez and Affleck became “Bennifer”, one of the first great portmanteau romances of the modern tabloid age. Their every movement was photographed. Their engagement ring was examined like a royal jewel. Affleck appeared in the Jenny from the Block video, and even ordinary gestures of affection became public entertainment.

They became engaged in 2002. They postponed their 2003 wedding amid extraordinary media attention. By early 2004 they were finished.

Lopez did what she has often done after emotional collapse. She moved. Within months she married Marc Anthony, a man she had known for years and with whom she shared both Latin heritage and musical chemistry. The marriage lasted considerably longer than her earlier unions. Their twins, Max and Emme, were born in 2008. The couple separated in 2011 and eventually divorced in 2014, remaining connected as co-parents.

There were other relationships. Dancer Casper Smart became a significant companion after the Marc Anthony separation. Later came former baseball star Alex Rodriguez. Lopez and Rodriguez looked, for a time, almost commercially perfect together: two disciplined, physically immaculate celebrities who understood fame, business and ambition. They became engaged in 2019. The wedding never happened. In April 2021 the relationship ended.

Then the impossible happened. Ben Affleck returned. Nearly twenty years after their first engagement collapsed, Lopez and Affleck were photographed together again. The old romance revived with extraordinary speed. They travelled together, appeared publicly as a couple, became engaged for the second time and married in Las Vegas in July 2022 before holding another ceremony in Georgia. For those who believe romance should have symmetry, it was irresistible. The great unfinished love story had completed its circle.

Except life is rarely interested in symmetry. By April 2024 they had privately separated. Lopez filed for divorce in August of that year. Their divorce was finalised in January 2025 and they became legally single the following month. By 2026 they were no longer husband and wife, though public appearances surrounding shared professional projects showed a relationship far less theatrical than the frenzy that once accompanied “Bennifer”.

One could make cheap comedy from four marriages and several broken engagements. Lopez has often been treated that way. Yet the more interesting question is why a woman who possesses wealth, discipline, admiration, beauty, children, international fame and extraordinary professional control has repeatedly placed such faith in romantic permanence.

Perhaps because love has always occupied an unusually important place in her imagination. She has rarely behaved like the cynical celebrity who keeps romance safely compartmentalised. She commits. She marries. She becomes engaged. She writes albums about relationships. She builds films around them. She has repeatedly made the private dream public, then discovered that publicity cannot protect it.

This is where Ain’t It Funny becomes more than an old hit. The original version did not even become the song most Americans remember under that title. In 2002, Ain’t It Funny was radically reinvented as the “Murder Remix” featuring Ja Rule and Caddillac Tah. It was not really a conventional remix at all. The music and lyrics were substantially new, built around hip-hop production and a reworking of Craig Mack’s Flava in Ya Ear.

That reinvention tells us something about Lopez herself. She has survived by refusing to remain one version of Jennifer Lopez. She was a dancer, then actress, then singer, then fashion figure, then perfume empire, then television personality, producer, Las Vegas performer and businesswoman. Each time the culture appeared ready to file her under an old category, she found another stage.

There were controversies along the way. Her vocal ability has been debated for years, sometimes with a degree of hostility rarely applied to male entertainers whose principal strengths also lie in performance rather than virtuoso singing. The “I’m Real” remix drew criticism for its use of a racial slur. Her Motown tribute at the 2019 Grammys produced criticism from viewers who questioned why a Puerto Rican-American performer had been chosen to lead a celebration of a historically Black label. She has endured mockery over Gigli, criticism of her romances, endless discussion of her appearance and the familiar accusation levelled at powerful female stars that ambition itself is somehow evidence of vanity.

Yet she remains. That may be the most striking fact of all. At an age when earlier generations of actresses were expected to disappear gracefully into supporting roles, Lopez has continued to present herself as glamorous, sensual and physically commanding. She has never treated desirability as something reserved for youth. Nor has she pretended that ageing does not exist. Rather, she has made discipline part of her identity: dance, exercise, diet, skin, clothes, posture, rehearsal.

Her sexuality has therefore remained part of the public image without becoming the whole of it. There is something highly controlled about Lopez's sensuality. She reveals, but seldom appears exposed. She understands exactly how much glamour depends upon withholding as much as displaying. The body is part of the performance, but the performer remains in command.

It is easy to call Jennifer Lopez sexy. It is more useful to ask why she has remained so. The answer is not simply her face or figure. It is appetite. She has appetite for work, love, performance, reinvention and life itself. She has repeatedly risked embarrassment because she prefers belief to detachment. There is something almost Victorian in that emotional extravagance: the conviction that love ought to be enormous, that the stage ought to be bright, that clothes ought to matter, that heartbreak ought to hurt and that after heartbreak one ought to dress beautifully and go out again.

That woman was already present in Ain’t It Funny. Herb Ritts placed her on a road and sent her towards a fortune-teller. She encountered prophecy, transformation, dance and romance. The imagery was theatrical, but the instinct was accurate. Jennifer Lopez has spent much of her life walking towards whatever comes next with the faith that the next love, next song, next film or next reinvention may finally complete the story.

It never does. Perhaps that is why the story continues.

Twenty-five years after Ain’t It Funny, the song feels less like a relic of early-2000s pop than an accidental commentary on the woman who sang it. Jennifer Lopez has gained almost everything fame can give, and learned repeatedly that fame cannot make affection permanent. She has married, divorced, loved, separated, returned to an old love, married him at last and lost him again. And still she works. Still she dances. Still she walks into the light.

Ain’t it funny.