Leo was photographed on the red carpet with his mum Irmelin ahead of the ceremony in Beverly Hills. The glamorous blonde often accompanies Leo to awards events, and she proved to be a lucky charm on the night as her handsome son picked up the award for Best Performance by an Actor in a comedy or musical for The Wolf of Wall Street.
On the red carpet, they bumped into Leo's good friend Bradley, who was joined by his mother Gloria. Following the ceremony, the foursome celebrated together at The Weinstein Company & Netflix Golden Globes afterparty.
Leo and Bradley have been friends for years – they first met in their twenties when Bradley worked as a doorman at a New York hotel and helped Leo to his room. At the time, the actor was riding high on the success of Titanic while Bradley was enrolled at the Actors Studio.
Since then, they have become good pals, holidaying together as well as partying on a number of occasions, and Bradley was no doubt delighted by Leo's Golden Globes success for his role in The Wolf of Wall Street.
While much has been made of the hedonistic film, Leo said his mother and father George were not fazed by his performance.
"I'm almost 40-years-old now, so I'd hope that I wouldn’t have to answer to them," he told Vanity Fair.
"I think that the perception of me is still the child actor. So that, you know, people would wonder what my parents thought.
"But to tell you the truth, it didn't faze them whatsoever. I mean, I was reading underground comics in the back of my dad's station wagon that were much more gratuitous that this at 10 years old, so nothing really affected them on that level."