Hollywood has produced plenty of unforgettable romances—but some famous pairings have practically vanished from pop culture memory. From whirlwind flings and broken engagements to relationships that once seemed destined to last, these celebrity couples prove that dating history in the spotlight can get surprisingly strange.

Cindy Crawford and Richard Gere

In the early 1990s, Cindy Crawford and Richard Gere were one of Hollywood’s most glamorous pairings. The supermodel and the Pretty Woman star married in 1991 after a whirlwind romance, despite a substantial age difference and enormous media attention. Their marriage lasted only a few years, and they divorced in 1995. Crawford later married businessman and former model Rande Gerber, while Gere eventually found lasting love with Alejandra Silva. Looking back, Crawford and Gere can feel like an unlikely pairing precisely because both became so strongly associated with different chapters of their lives. Their brief marriage, however, remains one of the era’s most memorable celebrity relationships. Gere turned 77 in August 2026.

Val Kilmer and Cher

Val Kilmer and Cher had a surprisingly intense romance in the 1980s. Their relationship reportedly began after they met through mutual friends, and the two quickly became close. Cher later recalled their connection warmly, even though it was relatively short-lived. Kilmer was still building his reputation as a major Hollywood leading man at the time, while Cher was already an established superstar. The pairing made sense in retrospect: both were charismatic, unconventional and completely comfortable standing out from the crowd. Kilmer went on to become famous for roles in Top Gun, The Doors and Batman Forever. He died in April 2025 at age 65, making this relationship part of a very different chapter of his life.

Cameron Diaz and Matt Dillon

Before Cameron Diaz became one of Hollywood’s biggest comedy stars, she was romantically involved with Matt Dillon. The pair met while working in the 1990s and eventually began dating. Their relationship lasted several years, with the two appearing together during a period when both were major names in the entertainment industry. They ultimately split before Diaz’s career reached another level with films such as There’s Something About Mary and Charlie’s Angels. Dillon later spoke respectfully about the relationship, while Diaz eventually stepped away from acting for a quieter family life. Because both stars later became associated with very different careers and personal lives, their time together is easy to overlook today.

Madonna and Tupac Shakur

Madonna and Tupac Shakur might sound like a pairing invented for a Hollywood screenplay, but their relationship was real. The pop superstar and the legendary rapper became romantically involved in the early 1990s, during a period when both were at enormous cultural peaks. Madonna later confirmed the relationship, putting to rest years of speculation surrounding the unlikely couple. Their romance was reportedly complicated by the intense scrutiny surrounding both stars and Tupac’s legal troubles. Shakur was killed in Las Vegas in 1996 at just 25, while Madonna continued building one of the longest careers in pop history. Their brief relationship remains one of the most unexpected celebrity pairings of the 1990s.

Tom Cruise and Cher

Tom Cruise and Cher may seem like they belong to completely different celebrity worlds, but the two actually dated in the 1980s. They met around the time of Madonna and Sean Penn’s wedding in 1985 and developed a romantic connection afterward. Cruise was already becoming a major movie star, while Cher was an established singer, actress and pop-culture icon. Their relationship did not last long, but Cher has spoken positively about Cruise over the years. She even included him among people she had dated when discussing her romantic history. Considering the wildly different public personas the two developed later, it is easy to forget that Hollywood once paired them together.

Julia Roberts and Matthew Perry

Julia Roberts and Matthew Perry had a short but memorable romance in the mid-1990s. Their connection began around the time Roberts appeared on Friends, where Perry was already becoming famous as Chandler Bing. The two reportedly dated for several months, and Perry later wrote about the relationship in his memoir. Roberts went on to become one of Hollywood’s most successful actresses, while Perry became permanently associated with Friends. Perry died in October 2023 at age 54. Their relationship is particularly interesting because it happened just as both stars were becoming major forces in entertainment, making it a fascinating snapshot of Hollywood before either career had reached its eventual peak.

Keira Knightley and Jamie Dornan

Before Jamie Dornan became internationally famous as Christian Grey in Fifty Shades of Grey, he was dating Keira Knightley. The two reportedly met in the early 2000s and began a relationship while their careers were still developing. Knightley was becoming known for films such as Bend It Like Beckham and Pirates of the Caribbean, while Dornan was working as a model and beginning his acting career. They eventually went their separate ways, with Knightley finding lasting love with musician James Righton and Dornan marrying actress Amelia Warner. Their early relationship is now an intriguing piece of both stars’ pre-fame histories.

Ryan Reynolds and Alanis Morissette

Ryan Reynolds and Alanis Morissette were once engaged, making their former relationship particularly surprising today. The pair began dating in the early 2000s and became a fixture at Hollywood events. They announced their engagement in 2004, but eventually ended the relationship in 2007. Reynolds later married Scarlett Johansson and then Blake Lively, while Morissette married rapper Mario Treadway and built a family of her own. Looking back, Reynolds and Morissette seem like an unusual match, but they reportedly shared a strong connection during their years together. Their engagement lasted several years before the couple ultimately decided they were better off apart.

Justin Timberlake and Jenna Dewan

Long before Jenna Dewan became closely associated with Channing Tatum, she reportedly had a brief connection with Justin Timberlake. The two were linked around the early 2000s, when Timberlake was transitioning from *NSYNC heartthrob to solo superstar. Dewan was still establishing herself as an actress and dancer. The romance was never a major long-term relationship, which may explain why it has faded from public memory. Timberlake eventually married Jessica Biel, while Dewan married and later divorced Channing Tatum before building a new family with Steve Kazee. It is one of those short Hollywood connections that becomes much more interesting once both people become household names.

Jennifer Garner and Scott Foley

Before Jennifer Garner became one of Hollywood’s most recognizable actresses, she was married to Scott Foley. The two met while working on Felicity and began dating soon afterward. They married in 2000, but their marriage ended in divorce in 2004. Garner later became part of another highly publicized Hollywood marriage when she married Ben Affleck. Foley, meanwhile, continued building a successful television career, including prominent roles on Scandal and other series. Their relationship is easy to forget because Garner’s later personal life attracted much more attention. Still, Foley was an important part of her early adult life, long before she became synonymous with roles in blockbuster films and major television projects.

Sofia Coppola and Quentin Tarantino

Sofia Coppola and Quentin Tarantino are better known today as influential filmmakers, which makes their past relationship especially unexpected. The pair were romantically linked during the 1990s, around the time both were establishing their distinctive creative identities. Coppola eventually became an acclaimed director known for films such as The Virgin Suicides, Lost in Translation and Marie Antoinette. Tarantino became one of the most recognizable directors of his generation through movies including Pulp Fiction and Kill Bill. Their relationship did not last, but the fact that two filmmakers with such unmistakable artistic styles once dated makes this pairing one of Hollywood’s more fascinating forgotten connections.

Cameron Diaz and Jared Leto

Cameron Diaz and Jared Leto were romantically involved in the late 1990s and early 2000s, long before either became associated with their later partners. Diaz was rapidly becoming one of Hollywood’s biggest stars, while Leto was balancing acting with his growing career as the frontman of Thirty Seconds to Mars. The two reportedly dated for several years and occasionally appeared together publicly. Their relationship eventually ended, and both moved on to very different personal and professional chapters. Diaz later married musician Benji Madden, while Leto remained famously private about his romantic life. Their pairing now feels like a particularly 1990s celebrity time capsule.

Jennifer Aniston and Tate Donovan

Jennifer Aniston and Tate Donovan actually experienced a particularly awkward Hollywood twist after their breakup: they had to play romantic partners on Friends. The two met in the 1990s and became engaged, but eventually ended their relationship. Donovan later appeared on Friends as Joshua, the character who became Rachel Green’s love interest. Aniston was still processing their breakup when they began filming together, making the situation considerably more complicated than it looked on screen. Aniston later became one of television’s most famous stars, while Donovan continued working successfully as an actor and director. Their real-life romance remains one of the more fascinating pieces of Friends history.

Elisabeth Moss and Fred Armisen

Elisabeth Moss and Fred Armisen seemed like an unusual pairing from the start, but they eventually married. The two met through the entertainment industry and became a couple before tying the knot in 2009. Their marriage lasted less than a year, and they divorced in 2011. Moss later became one of television’s most acclaimed dramatic actresses through projects such as Mad Men and The Handmaid’s Tale. Armisen continued his comedy career through Portlandia, Saturday Night Live and numerous other projects. Because their marriage was so brief and both developed very distinct careers afterward, their relationship can easily disappear from memory.

Taylor Swift and Taylor Lautner

Taylor Swift and Taylor Lautner dated in 2009, creating one of the most memorable all-Taylor celebrity couples. Their relationship reportedly began after they worked together on the film Valentine’s Day. Swift was already a major music star, while Lautner was at the height of his Twilight fame. Their romance was brief, but it generated plenty of attention because both were among the entertainment industry’s biggest young stars. Lautner later married Taylor Dome, while Swift went through several highly publicized relationships before continuing her record-breaking music career. The pair have since appeared to remain friendly, making their short romance feel more like a fun pop-culture footnote than a dramatic Hollywood breakup.

Janet Jackson and Matthew McConaughey

Janet Jackson and Matthew McConaughey reportedly had a brief romantic connection after meeting at the Grammy Awards in the early 2000s. The pairing sounds unusual now because their careers developed in such different directions: Jackson remained a music icon, while McConaughey became one of Hollywood’s most recognizable actors. McConaughey has suggested over the years that there was genuine chemistry between them, though the relationship was short-lived. Jackson eventually married Wissam Al Mana and welcomed a son, while McConaughey married model Camila Alves. Their brief connection is exactly the kind of celebrity romance that can disappear from memory once both stars move into entirely different chapters.

Ryan Gosling and Sandra Bullock

Ryan Gosling and Sandra Bullock dated in the mid-1990s after meeting while working together on Murder by Numbers. At the time, Gosling was still years away from becoming the romantic leading man associated with films such as The Notebook and La La Land. Bullock was already a major star. Their relationship reportedly lasted around a year, and both later moved on without much public drama. Bullock eventually became a mother and longtime partner of photographer Bryan Randall, while Gosling married Eva Mendes and started a family. Knowing what both stars became makes their early relationship especially fascinating—and surprisingly easy to forget.

Lisa Marie Presley and Nicolas Cage

Lisa Marie Presley and Nicolas Cage had one of Hollywood’s strangest celebrity marriages. The daughter of Elvis Presley married Cage in 2002, only a short time after their relationship became public. Their marriage lasted just a few months before Cage filed for divorce. Presley had already experienced several major relationships and marriages, while Cage had become one of Hollywood’s most recognizable actors. Presley died in 2023 at age 54, while Cage continues to work in film. Their brief marriage remains memorable because of the sheer combination of celebrity lineage and Hollywood eccentricity involved.

Jennifer Aniston and Adam Duritz

Jennifer Aniston and Counting Crows frontman Adam Duritz were briefly linked in the mid-1990s. Their relationship came before Friends transformed Aniston into a global superstar, making it easy to forget that the actress once dated the alternative-rock singer. Duritz was already known for his distinctive voice and the success of Counting Crows, while Aniston was still on the verge of becoming one of television’s biggest stars. The relationship did not last long, and both eventually moved on. Duritz later became known more for his music career than his celebrity relationships, while Aniston’s romantic history became a recurring part of tabloid culture.

John Krasinski and Rashida Jones

John Krasinski and Rashida Jones reportedly dated before either became firmly established in the roles that would define them. Krasinski was on his way to becoming Jim Halpert on The Office, while Jones was developing her career as an actress and writer. Their relationship was relatively brief, but it is an amusing piece of television history because both eventually became associated with beloved sitcom characters. Krasinski later married Emily Blunt, while Jones remained focused on acting, writing and producing. Their romance may not have lasted, but it happened during the early stages of two careers that would eventually become much bigger than either actor could have predicted.

Mila Kunis and Macaulay Culkin

Mila Kunis and Macaulay Culkin began dating in 2002, when Kunis was still best known for That ’70s Show and Culkin was already famous from Home Alone. Their relationship lasted roughly eight years, making it far more substantial than many people realize. The couple largely avoided the spotlight and rarely discussed their private life publicly. They eventually separated around 2010. Kunis later married Ashton Kutcher, while Culkin married actress Brenda Song. Because both stars became associated with very different eras of Hollywood, their long relationship is one of those celebrity romances that can surprise even longtime fans.

Bradley Cooper and Renée Zellweger

Bradley Cooper and Renée Zellweger were a couple for several years after meeting while working on Case 39. They began dating around 2009 and remained together until 2011. At the time, Zellweger was already an established Oscar-winning actress, while Cooper was entering the phase of his career that would turn him into a major leading man. Both later experienced dramatic professional transformations. Cooper became an actor, director and filmmaker associated with projects such as A Star Is Born, while Zellweger returned to the spotlight with Judy and other acclaimed roles. Their relationship was relatively private, which probably explains why it is often overlooked today.

Jason Schwartzman and Zooey Deschanel

Jason Schwartzman and Zooey Deschanel were briefly one of indie Hollywood’s most recognizable couples. Their relationship took place in the early 2000s, when both were building reputations for quirky, distinctive performances. Schwartzman was already known for films such as Rushmore and later became a frequent collaborator with Wes Anderson. Deschanel became a major television star through New Girl and continued making music with She & Him. They eventually went their separate ways, but their pairing feels almost perfectly suited to the alternative-Hollywood aesthetic of the era. It is the kind of relationship that makes fans wonder how they somehow forgot it happened.

John Mayer and Jessica Simpson

Jessica Simpson and John Mayer were involved in one of the more heavily scrutinized celebrity relationships of the 2000s. They began dating around 2006, following Simpson’s highly publicized marriage to Nick Lachey. Mayer’s reputation as a musician and Simpson’s status as a pop star and reality-TV personality made the pairing a regular tabloid subject. Their relationship was on and off before eventually ending. Simpson later married Eric Johnson and built a major fashion business, while Mayer continued his music career. Their romance now feels like a very specific snapshot of the mid-2000s celebrity culture, when paparazzi and tabloids closely followed almost every famous couple.

Scarlett Johansson and Josh Hartnett

Scarlett Johansson and Josh Hartnett dated after meeting while filming The Black Dahlia in the mid-2000s. Both were rising stars at the time, and their relationship attracted considerable attention. Hartnett had become famous through films such as Pearl Harbor and Black Hawk Down, while Johansson was rapidly becoming one of Hollywood’s most sought-after actresses. They eventually broke up, with Hartnett later stepping back somewhat from the Hollywood spotlight. Johansson went on to become one of the world’s highest-profile actresses, particularly through the Marvel franchise. Their relationship now belongs to an earlier chapter of both careers.

Kat Dennings and Josh Groban

Kat Dennings and Josh Groban surprised fans when they began dating in the early 2010s. Dennings was known for her comedic roles, particularly 2 Broke Girls, while Groban had built a successful career as a singer and performer. The two were photographed together frequently and seemed genuinely affectionate, but their relationship lasted only a couple of years. They eventually separated and moved on with their respective careers. Groban continued performing around the world, while Dennings continued acting in television and film. Because their personalities seemed so different on paper, their relationship remains one of those celebrity pairings that people often forget ever happened.

Michelle Rodriguez and Cara Delevingne

Michelle Rodriguez and Cara Delevingne were briefly one of the most talked-about celebrity couples of the mid-2010s. The Fast & Furious actress and British model became romantically linked in 2014 and were photographed together during vacations and public outings. Their relationship attracted attention partly because both women were major fashion and entertainment figures with very different public images. The romance eventually ended, and both continued building independent careers. Delevingne later expanded into acting, while Rodriguez remained a fixture of major action franchises. Their brief relationship now feels like a snapshot of a particularly candid era of celebrity culture.

Leighton Meester and Sebastian Stan

Leighton Meester and Sebastian Stan met while working on Gossip Girl, where they played characters whose complicated relationships unfolded on screen. Off camera, the two became a real-life couple. They dated for several years before splitting around 2010. Meester later married actor Adam Brody, while Stan went on to become a major Marvel star through his role as Bucky Barnes. Their relationship is especially easy to forget because both actors later became strongly identified with different projects. For fans of Gossip Girl, however, their romance remains a memorable example of a television pairing becoming real behind the scenes.

Nicole Kidman and Lenny Kravitz

Nicole Kidman and Lenny Kravitz were once engaged, making their past relationship especially surprising. The actress and rock musician dated in the early 2000s, and Kidman later confirmed that they became engaged. Their relationship ended before they reached the altar, but they remained on good terms. Kidman later married Keith Urban, while Kravitz continued his music career and became a respected actor in his own right. Kravitz’s daughter, Zoë Kravitz, later worked with Kidman on Big Little Lies, adding an amusing Hollywood connection to the story. Kidman has spoken positively about her former relationship with Kravitz.

Jennifer Aniston and Vince Vaughn

Jennifer Aniston and Vince Vaughn became a couple after meeting while filming The Break-Up in 2005. Their relationship quickly attracted attention because Aniston had recently gone through her highly publicized divorce from Brad Pitt. Vaughn was already one of Hollywood’s most recognizable comedy stars. The two kept much of their relationship private, but they eventually separated in 2006. Despite the breakup, they continued promoting their movie professionally. Aniston later became linked to several other major celebrities, while Vaughn continued his successful comedy career. Their romance is now remembered almost as an extension of the mid-2000s Hollywood era that produced The Break-Up itself.

Liv Tyler and Joaquin Phoenix

Liv Tyler and Joaquin Phoenix dated while filming Inventing the Abbotts in the 1990s. Both were young actors developing impressive careers, and their relationship reportedly became serious during production. Tyler later described Phoenix as one of her closest friends, even after their romance ended. Phoenix went on to become an Oscar-winning actor through films including Walk the Line and Joker, while Tyler became known for projects such as The Lord of the Rings. Their relationship is particularly memorable because the two had strong chemistry on screen and remained connected professionally and personally after their breakup.

Ashley Olsen and Lance Armstrong

Ashley Olsen and cyclist Lance Armstrong became romantically linked in 2007, creating an age-gap relationship that received plenty of media attention. Olsen was already famous from childhood through her television career and fashion ventures, while Armstrong was one of the most recognizable athletes in the world. Their relationship was relatively brief and generated substantial tabloid interest before ending. Olsen later focused heavily on her fashion career and private life, while Armstrong’s public reputation underwent major changes because of his doping scandal. Their romance therefore belongs to a very different chapter of both lives—and is often forgotten amid everything that happened afterward.

Drew Barrymore and Christian Bale

Drew Barrymore and Christian Bale reportedly went on a date when they were young actors, long before either had reached their adult career heights. The connection was brief, but Bale has spoken about Barrymore warmly when recalling their early years in Hollywood. Barrymore went on to become a major actress, producer and talk-show host, while Bale developed into one of his generation’s most respected dramatic performers. Their story is less about a serious romance and more about two future Hollywood heavyweights crossing paths before their careers exploded. That early connection makes it a fun piece of celebrity trivia.

Katie Holmes and Jamie Foxx

Katie Holmes and Jamie Foxx were linked for years before they publicly acknowledged the relationship. The pair reportedly became close after Holmes’ divorce from Tom Cruise, and they were photographed together on several occasions. For much of their relationship, however, both stars kept their private lives away from the spotlight. They eventually separated around 2019. Holmes later continued acting and directing, while Foxx remained one of Hollywood’s most versatile entertainers. Their relationship is easy to overlook because so much of it happened quietly, but it was one of the entertainment industry’s most persistent celebrity mysteries for several years.

Rachel Bilson and Bill Hader

Rachel Bilson and Bill Hader had a short-lived romance that surprised fans because of their very different public personas. The O.C. actress and Saturday Night Live alum were linked in 2019 after working together on The To Do List. They appeared together publicly and seemed comfortable as a couple, but the relationship did not last long. Hader continued his acclaimed work on Barry and other projects, while Bilson remained active in television and podcasting. Because the relationship happened relatively quietly and ended without major drama, it has since become one of those celebrity romances that can easily slip out of public memory.

Brad Pitt and Christina Applegate

Before Brad Pitt became one of Hollywood’s biggest stars, he had a brief connection with Christina Applegate. The two attended the 1989 MTV Video Music Awards together, but the evening did not exactly go according to plan. Applegate later revealed that she left Pitt during the event and went off with another rock star. Pitt was reportedly unhappy about the situation, and the story became one of those legendary early-Hollywood dating anecdotes. Applegate later explained the episode publicly, giving fans a rare glimpse into Pitt’s life before superstardom. Their relationship was brief, but the story has lasted far longer than the romance itself.

Rihanna and Shia LaBeouf

Rihanna and Shia LaBeouf reportedly went on one date in 2007, making this less a conventional relationship and more a bizarre celebrity footnote. LaBeouf later said that the two met after communicating about getting together and eventually went out, but that the chemistry simply was not there. Rihanna went on to become one of the biggest music and fashion figures in the world, while LaBeouf developed a career spanning major studio films and more unconventional projects. Because there was apparently only one date, this pairing is particularly easy to forget—but also exactly the sort of unexpected celebrity connection that makes dating-history lists so entertaining.

Nick Lachey and Kim Kardashian

Before Kim Kardashian became the center of a global reality-TV empire, she briefly went on a date with Nick Lachey. The connection happened in the mid-2000s, after Lachey’s highly publicized divorce from Jessica Simpson. Kardashian was still emerging as a celebrity at the time and was not yet the billionaire businesswoman she would become. Lachey later recalled the date publicly, describing the paparazzi attention surrounding their outing. Kardashian eventually married Kanye West and later built major businesses including SKIMS, while Lachey continued his music and television career with wife Vanessa Lachey. Their brief encounter feels like a snapshot of Kardashian’s pre-Keeping Up With the Kardashians years.

Brad Pitt and Gwyneth Paltrow

Brad Pitt and Gwyneth Paltrow were one of Hollywood’s defining young couples of the 1990s. They met while working on Se7en and began dating in 1994. Their relationship became serious enough that Pitt and Paltrow became engaged in December 1996, but they broke up roughly six months later. At the time, both were rapidly becoming major stars, and their glamorous image made them a favorite of entertainment magazines. Paltrow later described Pitt affectionately and has spoken about how young they both were. Pitt eventually married Jennifer Aniston and Angelina Jolie, while Paltrow built a career as an actress and entrepreneur.

Axl Rose and Stephanie Seymour

Axl Rose and supermodel Stephanie Seymour became one of rock music’s most recognizable couples in the early 1990s. Seymour appeared in Guns N’ Roses videos including Don’t Cry and November Rain, making their relationship part of the band’s visual identity. The pair became engaged, but their relationship ended in 1993. Their breakup was followed by serious allegations and legal disputes, which were eventually settled. Rose continued performing with Guns N’ Roses, while Seymour remained an influential figure in fashion. Their romance is especially memorable because Seymour’s appearances in the band’s videos became closely associated with one of the most recognizable eras in rock history.

Johnny Depp and Winona Ryder

Johnny Depp and Winona Ryder were one of the quintessential celebrity couples of the early 1990s. They met while working around the time of Edward Scissorhands, began dating, and quickly became one of Hollywood’s most photographed young couples. Depp famously became engaged to Ryder, and the relationship inspired enormous media attention. They eventually split in 1993, but their connection remained a defining part of both stars’ early careers. Ryder continued starring in acclaimed films before later enjoying another career resurgence with Stranger Things. Depp went on to become one of the world’s most famous actors. Their relationship remains one of Hollywood’s most recognizable forgotten romances.

Leonardo DiCaprio and Gisele Bündchen

Leonardo DiCaprio and Gisele Bündchen were one of the defining celebrity couples of the early 2000s. The Oscar-winning actor and Brazilian supermodel began dating around 2000 and remained together on and off for several years. They were frequently photographed at glamorous events and vacations, creating an image that seemed almost too perfectly Hollywood. The relationship ended for good around 2005. Bündchen later married NFL star Tom Brady, while DiCaprio continued his long-running reputation for dating high-profile models and actresses. Looking back, their relationship represents an era when two of the world’s biggest young stars were constantly appearing together in entertainment headlines.

George Clooney and Talia Balsam

Before George Clooney became famous for insisting he would never marry again—before eventually doing exactly that—he was married to actress Talia Balsam. The couple tied the knot in 1989, when Clooney was still establishing himself as an actor. Their marriage ended in divorce in 1993. Clooney later became one of Hollywood’s most famous bachelors before marrying international human-rights lawyer Amal Alamuddin in 2014. Balsam continued a successful acting career, including a prominent role on Mad Men. Because Clooney’s later bachelor years became such a major part of his public image, his first marriage is surprisingly easy to overlook.

Robert Downey Jr. and Sarah Jessica Parker

Robert Downey Jr. and Sarah Jessica Parker were a serious couple during the 1980s and early 1990s. They began dating when both were young actors and remained together for several years. Parker later discussed the difficulties of being in a relationship while Downey struggled with substance abuse, while Downey has credited Parker with caring deeply about him during that period. Eventually, the relationship ended and both built very different lives. Parker became synonymous with Sex and the City, while Downey later achieved an extraordinary career resurgence and became one of Hollywood’s highest-paid stars through Marvel. Their long early relationship is often overshadowed by everything that came afterward.

Sarah Jessica Parker and John F. Kennedy Jr.

Sarah Jessica Parker and John F. Kennedy Jr. briefly dated in the early 1990s, creating a pairing that feels almost tailor-made for a Hollywood history book. Parker was a rising actress who would later become globally famous as Carrie Bradshaw, while Kennedy was one of America’s most recognizable public figures. Their relationship reportedly lasted around six months and attracted considerable attention because Kennedy’s private life was closely watched. Parker later described the intense public scrutiny surrounding the relationship. Kennedy eventually married Carolyn Bessette, while Parker married Matthew Broderick. Kennedy died in a plane crash in 1999, at age 38.