The oddest couples to ever walk down the Oscars’ red carpet

WHAT’S the most interesting part of every A-lister’s outfit as they traverse the Oscars red carpet each year? The arm candy, of course.

Angelina Jolie, James Haven

WHAT’S the most interesting part of every A-lister’s outfit as they traverse the Oscars red carpet each year? Forget the gown and the jewels, it’s all about the arm candy.

We’ve travelled through time with the ghost of Oscars past to scope out questionable red carpet pairings of the most awkward-looking A-listers of all time.

From surprisingly close siblings like Angelina and her brother James, to iconic 80s couple Michael Jackson and Brooke Shields, these are the twosomes you didn’t see coming ... and those we wish were still an item.

You know they feel as awkward as they look.

Brooke and Michael

Remember Brooke Shields and Michael Jackson’s fleeting relationship in 1981? Jackson met the 15-year-old Shields that night and the pair dated after that. Shields spoke emotionally at the King of Pop’s memorial, saying theirs was “the most natural and easiest of friendships”.

“Both of us needed to be adults very early but when we were together, we were two little kids having fun,” she said.

Ange’s brotherly love

Angelina Jolie and James Haven at the 72nd Annual Academy Awards in 2000. Picture: Getty/Corbis

If Oscar-winner Angelina Jolie and her brother James Haven look close, it’s because they are. But although at the time the world was shocked by their passionate kiss on the red carpet, the reality was much more innocent.

The siblings had arrived together after visiting their mother Marcheline, who was spending her first day in hospital for cancer treatment. She died in 2007.

A family friend told RadarOnline: “The day she kissed Jamie at the Oscars, it was the first day Marcheline was treated for cancer. They left the hospital together and got ready together,” she said.

Julia and Kiefer

What about the it couple of the early 90s?

Julia Roberts and Kiefer Sutherland met on the set of their 1990 movie Flatliners and quickly fell in love.

But it soon turned to heartbreak when Roberts called off their engagement just a few days before the wedding. Rumours claim it was Sutherland’s wandering eye that caused the rift.

Roberts kicked him to the side and moved on with his Lost Boys co-star Kason Patric.

There are no hard feelings though. Sutherland later said of the breakup: “I commend Julia for seeing how young and silly we were, even as painful and difficult as it was”.

Check out more in our gallery.

Oscars’ oddest pairings