And the Award for the Most Unusual Plus-Ones in Oscars History Goes To…

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Brangelina Oscars
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From the nominated films and red-carpet dresses to the outrageous afterparties, the Academy Awards are – without a doubt – the highlight of awards season. Having first started in 1929, the event is now in its 91st year, meaning there are nine decades of snubs, victories, wardrobe malfunctions, awkward kisses, and tearful acceptance speeches to sift through.

As the biggest night in Hollywood, invited guests have a lot to plan for: what they’ll wear, what they’ll say, and (most importantly) who they’ll bring as a date. After all, your support system is key on a night this momentous. While most reserve the coveted plus-one invite for their significant other, some take an alternative route and choose to bring a family member, a friend, or even inanimate objects. Discover seven such (unexpected) examples, below.

1

Most Adorable

Drew Barrymore and Her Mother

When Steven Spielberg’s E.T. was nominated for Best Picture in 1983, the opportunity for its young star, Drew Barrymore, to attend the Academy Awards arose. In what was one of the most adorable moments in red-carpet history, Barrymore attended the star-studded event in a pink princess gown alongside her mother, who wore a matching white fur shrug. Cue the heart-eyes emoji.

Drew Barrymore and Her mother at 1983 Oscars
Photo: Courtesy of Getty Images
2

Most Iconic

Jennifer Lopez and Ben Affleck

As you might expect, there are literally hundreds of iconic couple moments from the Oscars: Gwyn and Brad, Johnny and Winona, Tom and Nicole – the list goes on. However, the most iconic one came in 2003 when Jennifer Lopez and Ben Affleck hit the red carpet together.

We chose this for two reasons. Firstly, the fever pitch surrounding their relationship was entirely new for the times. In fact, many have called them “the first couple of the internet age”. Second, this was the first couple to spark a name mash-up, becoming known as the portmanteau “Bennifer”, which has since become a commonplace practice. The extreme overexposure that came as a result of mass media attention would eventually lead to the couple’s demise.

Jennifer Lopez and Ben Affleck
Photo: Courtesy of Getty Images
3

Most Unexpected

Brooke Shields and Michael Jackson

From Matthew Broderick tapping pal Helena Bonham Carter as his date to Cher and Val Kilmer’s brief but bizarre romance, there have been unexpected couples on the Oscars red carpet before. However, we weren’t expecting to find this one in the archives. Sure enough, Michael Jackson took Brooke Shields as his date to the Academy Awards in 1981, although the actress was only 15 years old at the time. The two enjoyed a close friendship for many years, but it was not thought to be a romantic relationship.

Michael Jackson and Brooke Shields at the Oscars
Photo: Courtesy of Getty Images
4

Most Supportive

Kate Winslet and Leonardo DiCaprio

Kate Winslet and Leonardo DiCaprio have stood by each other’s side, both metaphorically and physically, for the past 20 years at dozens of award ceremonies. Their platonic friendship is well documented, and the support they continually give each other is serious #FriendshipGoals.

They’ve been through a lot of ups and downs together, like the year when they were both snubbed by the Academy for their exemplary starring roles in Revolutionary Road. But in the same year, Winslet won an Oscar for Best Actress in The Reader. However, nothing could prepare us for the year that DiCaprio took Winslet to the Academy Awards as his date in 2016, and then ended up winning his first-ever statuette for The Revenant. Talk about a ride-or-die moment.

Leonardo DiCaprio and Kate Winslet
Photo: Courtesy of Getty Images
5

Most Familial

Jennifer Lawrence and Her Family

A lot of stars choose to bring mom, dad, or a sibling to the Oscars with them for emotional support. However, Jennifer Lawrence went a step beyond in 2013 when she brought her entire family to witness her big win for Silver Linings Playbook. Mom, dad, brothers, and sister-in-law were all present for her epic night.

Jennifer Lawrence and family at Oscars
Photo: Courtesy of Getty Images
6

Most Unconventional

Björk and a Giant Egg

Count on Icelandic musical savante Björk to upstage everyone on the list when it comes to unusual plus-ones. In 2001, she made red-carpet history by showing up in her now-legendary swan dress, but the picture wouldn’t be complete without the giant egg she brought with her as a companion to her outfit.

Bjork Swan dress Oscars egg
Photo: Courtesy of Getty Images
7

Most WTF

Angelina Jolie and James Haven

Angelina Jolie has been an Oscars red-carpet favorite for many years, but back in the day, her presence was always a cause for controversy. Everyone remembers what happened when she brought her brother James Haven to the Academy Awards in 2000. Because the moment was frozen in time by cameras, it probably looked worse than it was, but it’s still the most WTF moment in Oscars history because of how bizarrely it came off.

Angelina Jole and Brother at the Oscars
Photo: Courtesy of Getty Images
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