A Timeline Of Every Brad Pitt Red Carpet Date Explained

Brad Pitt is an award-winning actor who's won over audiences with stellar performances in films like A River Runs Through It, Fight Club, and Once Upon a Time ... in Hollywood. But he's also a headline-making star who's been involved in drama-filled romances with more than just a few famous actresses. Because of that, fans are always interested in what's going on in Pitt's personal life, and one way to get an indication of his current romantic status is to look at who he's bringing to red carpet events.

From his early days in the '80s to arriving at the premieres of his latest blockbuster productions, Pitt has always piqued the public's interest by arriving on scene with intriguing dates by his side. While you could surely name a few, including the showbiz icon's two equally famous ex-wives, there are probably others you've forgotten or simply never knew about in the first place. And although some of the dating situations were super sweet, others were sticky and downright scandalous.

Interested to find out more? Well, that's where we come in. Here's a timeline of Brad Pitt's red carpet dates, and why each woman (or family member) was lucky enough to score such a memorable and enviable invitation.

Back in 1988, Brad Pitt popped up with his first red carpet date, Shalane McCall, and kicked off a habit of bringing his onscreen partners (who were also reportedly his romantic partners) with him to major industry events. Early fans of Pitt may remember that he and McCall attended a screening of the CBS miniseries Windmills of the Gods in West Hollywood, where the two looked happy as could be in full view of the cameras. They also showed up together at a Valentine's Day gala that same year. Fresh-faced and always outfit-coordinated, the pair played the perfect match.

That's not surprising considering they were co-stars on Dallas, a show that cast him as Randy, the boyfriend of McCall's character, Charlie Wade. Fans were used to seeing them in a romance onscreen, but having met just "an hour" before shooting their first romantic scene together, McCall told People "it wasn't awkward," adding, "We were laughing and kidding around." 

Still, the fact they they were reportedly dating in real life was somewhat scandalous considering he was about 24 at the time and she was only 15! And, to be honest, this wasn't the only relationship that Pitt was supposedly involved in that featured an inappropriate (and illegal?) age gap. But more on that later.

That same year, Brad Pitt showed up on the red carpet with his Cutting Class co-star, Jill Schoelen, at premieres, as well as at the 20/20 Club in Los Angeles — which made them industry event staples for a brief time. While you may not remember their time together, Pitt and Schoelen were actually engaged by 1989 ... although it only lasted for three months before she supposedly broke up with him in a rather brutal way.

"[Schoelen] called me up in Los Angeles and was crying on the phone. She was lonely and there was a huge drama," Pitt later told The Sun (via CTV News). "At this point I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her." Explaining that he "went straight to the set where she was filming," the two later went out for dinner and that's when she gave him some unexpected news. "She told me that she had fallen in love with the director of the film," Pitt claimed. "I was so shocked I said, 'I'm outta here.'" 

So, not a happy ending. Frankly, Pitt's next red carpet date didn't turn out any better.

Brad Pitt's love life didn't improve that much when he decided to date actress Christina Applegate. The two were spotted at an Amnesty International Event together in 1988 before hitting the red carpet at the 1989 MTV Video Music Awards, which is where their relationship unexpectedly ended. 

In 2015, Applegate admitted to rumors that had buzzed about the incident for years. During an interview on Watch What Happens Live, the star confessed to host Andy Cohen that she happened to meet someone else at the event, and she must have found him more interesting than Pitt, because she ditched her date for the other dude. While the other fella was apparently famous, as well, Applegate wouldn't reveal who it was. We were more than prepared to do a little investigating ourselves by digging into the event's performers and presenters list — Applegate presented the best group video honor with Alice Cooper, for example, but we can't really see them together — but the mystery man in question publicly kissed and told about a year later. Calling their romance "a brief fling" during an appearance on Elliot in the Morning (via Yahoo! Entertainment), rocker-actor Sebastian Bach (a.k.a. Gil from Gilmore Girls) revealed, "That dude would be me."

It took about 25 years for that celeb dating mystery to be solved, but what we've long known is that Pitt went from being dumped by Applegate to the second of his scandalous relationships next.

After meeting on the set of Too Young to Die?, Brad Pitt and Juliette Lewis dated for three years in the early '90s and hit up plenty of red carpets together. The duo was seen at the premiere for Thelma and Louise, as well as for The Last of the Mohicans, just to name a couple, and later attended the 1992 Academy Awards with styles that very much suited their quirky relationship. With Pitt wearing a suit that featured unusual detailing around the neck, as well as white-topped shoes, Lewis opted for a gown that could have been mistaken for a wedding dress, which she paired with a pearl necklace that reached down to her legs and shiny white gloves. She topped off her look with cornrows that were entirely inappropriate for the star.

Speaking of inappropriate, it's impossible to mention Pitt and Lewis without pointing out that this was another questionable relationship due to the fact that, according to InStyle, she was around 17 when they got together and he was 27. In 2014, Lewis told People that in the past, anytime she ended up in the news, it was "usually about Brad Pitt or drug addiction," which she says she left behind long ago: "I'm 40. I quit all my bulls**t at 22. There is growth. Get out of the past." 

That's certainly something that Pitt found hard to do after the pair broke up, if a certain confession he later made was any indication...

Jitka Pohlodek may not be the most famous woman who ended up as one of Brad Pitt's red carpet dates, but she was apparently charming enough to accompany him to the Legends of the Fall premiere in 1994. The stunning Czech model and Sugar: The Fall of the West actress walked hand-in-hand with the actor, who was still sporting the kind of long, bleach-blond hair that he had grown for the film. The pair were perfectly coordinated with their boots and denim, which only bolstered the long-held notion that Pitt tends to morph into whatever lady he's dating.

But their looks weren't the only thing that brought these two beautiful people together. Pitt and Pohlodek also shared a love of animals. According to People, "Her two pet bobcats fit in nicely with his menagerie: three dogs — Todd Potter, Saudi, and Purty — and an assortment of chameleons and iguanas." Wait, bobcats?! Hopefully, they were kept far away from the lizards.

Despite the fact that they had a lot in common, Pitt and Pohlodek didn't make it in the long run, perhaps partially due to the fact that they were dating when he told Vanity Fair that he was still in love with Juliette Lewis. Awkward!

By 1996, Brad Pitt was showing up on red carpets with his fellow star and love at the time, Gwyneth Paltrow. During another transformation that saw him match his lady, Pitt chopped off his long hair and opted for a new 'do that was so close to Paltrow's it made the pair look like twins on the red carpet. The two showed off their matching style while attending multiple film premieres, as well as making a memorable appearance at the 68th Annual Academy Awards, which marked Pitt's first time at the Oscars. "Donning tiny oval sunglasses and a sleek suit, Brad looked cool, calm and collected as he made his way down the carpet. For her part, Gwyneth stunned in a sequined Calvin Klein slip dress, which is one of the actress' most glamorous red carpet looks to date," according to E! News.

While Pitt and Paltrow were certainly great for headlines and got engaged, the two split in 1997. Twenty years later, the actress opened up about what went wrong, telling Girlboss Radio that she was to blame. "I've f**ked up so many relationships," she confessed (via Page Six). Explaining that she's a good friend, sister, daughter, and mother, Paltrow admitted that she's at her "most vulnerable and f**ked up in the romantic slice of the pie." The Iron Man star then sent a message to her ex, saying, "So Brad Pitt, if you're listening. I f**ked that up, Brad."

After Brad Pitt's split from Gwyneth Paltrow, the actor whose star was continuing to rise reportedly dated his Meet Joe Black costar and onscreen love interest, Claire Forlani. In 1998, the two walked the red carpet together for the 50th Annual Writers Guild of America Awards but opted not to go overly formal with their outfits. He wore an all-black suit with what appeared to be a beanie, while she donned an oversized leather coat on top of a thin, flowy dress.

Over two decades after Meet Joe Black was released, Forlani, who is now married to Ever After and Mission: Impossible II actor Dougray Scott, talked about making out with Pitt onscreen. "Brad and I literally getting through every brand of mint, having to do that love scene that just went on for days and days and days," she told The Daily Telegraph with a laugh. "There wasn't a brand we didn't try ... I remember not being able to look at mints for about a year after doing that scene." 

Forlani may not have been able to look at mints, but we wonder if she still likes to look back on her red carpet date with her former costar. We could ask the same thing of the woman who came next in Pitt's life, one who's still stirring up headlines with the star to this day.

Brad Pitt had plenty of famous red carpet dates, but Friends star Jennifer Aniston is surely one of the most memorable. Married from 2000 to 2005, they were one of Hollywood's hottest couples throughout their relationship (and beyond, to be honest). Fans fawned over the pair during the early days of their romance, when he brought her as his date to the premiere of Fight Club in 1999. From there, the fabulous duo continued to make the rounds at industry events and seemed to always create an excited buzz regarding their A-list status and attractive attachment.

But it was probably their appearances during the awards seasons that stirred up the most attention, and even though they divorced years ago (and each remarried and split from their respective significant others), many fans would still love to see Pitt and Aniston get back together. Frankly, if the exes continue to appear thrilled to see each other the way they did at the 2020 Golden Globes, then who knows what might happen in the future.

Granted, any kind of rekindled romance would mean that the spouses-turned-friends would have to accept that there will always be someone else in Pitt's life: the woman who came after Aniston.

After Jennifer Aniston, there was Angelina Jolie. Or rather, there was Brangelina. Just one month after Aniston filed for divorce in 2005, Brad Pitt and Angelina Jolie were spotted on a beach together in Kenya with her son, Maddox, sparking rumors that the new relationship had started before Pitt's marriage to Aniston had even ended. Despite their bumpy beginning, Pitt and Jolie were soon showing up to red carpets arm-in-arm. Having celebrated the openings of multiple films between them, by 2007, the stars were one of the most talked-about pairs at the Golden Globes. Together, the actor and actress were seemingly always ready to pose for the cameras at events, showing off their sophisticated style that suited their roles as members of Hollywood's elite. 

In 2015, the newly married Pitt and Jolie made their last red carpet appearance together at the premiere of their film, By the Sea, which was just a year before she filed for divorce. While that ended Pitt's tendency to bring his romantic partners with him to red carpet-worthy events, there have been a few other special people in his life who have stepped up to accompany him to major showbiz occasions.

Brad Pitt may have taken a break from romance following his split from Angelina Jolie, but thankfully his mom and dad, Jane and William Pitt, have been willing to be his red carpet dates over the years. They were with him at The Devil's Own premiere in 1997, The Curious Case of Benjamin Button premiere in 2008, and at the Oscars in 2012. However, they haven't just been delegated to the roles of back-up dates. At times, they've even shown up when their son was accompanied by one of his famous ladies. At the premiere of The Devil's Own, Paltrow was also there, and during the latter two events, Jolie was with the formal family.

More recently, some fans thought that Pitt brought his mom to the 2020 Oscars, but the woman who was spotted beside him was actually his manager, Cynthia Pett-Dante. While she's surely a fine companion for an industry event, Pitt has shown up with a few other people who may just be his sweetest red carpet dates to date.

Brad Pitt's parents and wives aren't the only family members the star has brought along to the red carpet. In 2014, Pitt shared the limelight with three of his and Angelina Jolie's kids at the premiere of Unbroken. Maddox, Pax, and Shiloh all dressed in snazzy suits and posed with their dad for the cameras. The group was joined by Pitt's parents, William and Jane, who were there once again to support their son.

While the actor was still in a relationship with Angelina Jolie at the time, the actress was unable to attend the event with her husband, despite the fact that she was the one who had produced and directed the film. Unfortunately for the star, she had come down with the chickenpox and admitted, according to the Los Angeles Times, that she was instead "home, itching, and missing everyone." She may have been uncomfortable, but the Jolie-Pitt kiddos did a great job filling in for their mom and looked perfectly at ease spending time on the red carpet with their famous pops. 

Perhaps that means we'll see them with him again at an industry event sometime in the future — well, now that the post-divorce family drama has settled down and once he has a new film to promote, that is.