The 9 Most Questionable Golden Globes Dates

Stars’ plus-ones have long been a source of
questionable decision making at the awards show.
From barefoot acceptance speeches to P. Diddy, the
Globes’ alcohol enthusiast, the Golden Globes
Awards is no stranger to strangeness. Stars’ plus-
ones have long been a source of questionable
decision making at the awards show.
On Sunday, Jan. 11, celebs will hit the carpet with
dates in tow. Here’s a look back at some of the
most questionable pairs.

1. Angelina Jolie and Billy Bob Thornton
(2002). Long before Angie got chummy with Pope
Francis, she was better known for accessorizing with
vials of blood. Jolie and Billy Bob Thornton were
famous for packing on the red carpet PDA, although
in 2002 they cleaned up with coordinating black
satin. Never Forget.

2. Gwyneth Paltrow and Brad Pitt (1996). And long
before Brad Pitt was Mr. Angelina Jolie, he had a
host of interesting red carpet affairs. Pitt and then-
girlfriend Gwyneth Paltrow arrived at the Golden
Globes in 1996 in matchy-matchy black and white
outfits. We can’t decide which is a better ‘90s
statement: Brad’s sunnies or that oversized collar.
3. Nick Nolte and Vicki Lewis (1999). Those
coordinating red carpet glasses—need we say more?

4. Ben Affleck and Matt Damon (1998). Ah, one of
Hollywood’s longest running bromances. Matt
Damon’ spikey, bleached hair and Ben Affleck’s wide
black tie are what the ‘90s are made of.

5. Leonardo Dicaprio and his mom (1994). Leo is
known for his laundry list of supermodel dates, but
back in the day, he brought his mom to the awards
show. We can’t get enough of that sideswept hair
and textured vest.

6. Sharon Stone and her mom (2003). Sharon Stone
and her mom arrived at the Globes, both dressed
head-to-toe in black. The abundance of paradoxical
apparel happening here is almost admirable.

7. Helena Bonham Carter and mom (2011). Helena
Bonham Carter also brought her mom along. From
Carter’s mismatching shoes to her mom’s full-body
dress texture, it’s not hard to see where the offbeat
actress got her fashion sense.

8. Helena Bonham Carter and Tim Burton
(2013). Helena strikes again! These recent exes
were the face of eccentricity in Hollywood. This date
was just one of many curious—yet somehow
complementary—outings the couple went on.

9. Paz de la Huerta and date (2011). To be fair, this
was a post-Globes photo, but it is memorable
nonetheless. This questionable picture was captured
only moments before her dress gave way to a full-
on nip slip.
So which Golden Globe plus-one do you think is the
most questionable?