The Wolf of Wall Street star hosted Saturday Night Live for the third time on Jan. 25.
During his opening monologue, Hill gushed about being nominated for an Oscar in the comedy-crime flick, which tells the real-life story of Jordan Belfort, who scammed Wall Street's biggest investors. But Hill was quickly interrupted by an audience member and was asked what it was like to work with DiCaprio.
"Oh I wasn't really opening the floor for questions," the 30-year-old awkwardly responded. "Leo, which is short for Leonardo, you know, he's a terrific guy. He's still learning but he's obviously a huge star."
After answering inquiries about the accomplished thesp's "beautiful" hair and a question from his Moneyball costar Brad Pitt, Hill tried to boast about his acting abilities and one up the seemingly invincible DiCaprio.
"The truth is Leo wasn't even supposed to be in the movie," the Get Him to the Greek star revealed about the A-list actor.
He continued: "Okay, here's what happened. I call up . I say 'Marty, it's JH. I'm ready to get in the ring together.' He says 'finally.' And I say, 'should we get DiCaprio on board.' And Marty says, 'I don't know if he can handle it. Sure. He's a movie star. He puts teenage girls in the seats. But we need a real actor, like you.'"
And that's when DiCaprio crashed the monologue and received a thunderous applause from the audience, much to Hill's embarrassment.
"I have a question," DiCaprio said. "What the hell are you doing man?"
Hill bumbled over his words and tried to explain himself to DiCaprio.
"I was like this guy Leo taught me everything I know and I'd be nothing without him," Hill said sheepishly. "And he's such a model. Physically, like he has the looks of a model but also like a role model and really charitable, plus The Aviator."
But DiCaprio wasn't buying it and tried to lecture Hill about the importance of staying humble and not acting like a big shot in Hollywood.
"I'm just sorry, I just got so excited," Hill said to DiCaprio.
Hill then asked "Le" if they could "do the thing that we always did that made me feel safe."
DiCaprio agreed and Hill promptly outstretched his arms and took on Kate Winslet's role to reenact the iconic flying scene from Titanic.
"Am I flying Jack?" Hill asked DiCaprio, who was nuzzling his cheek.
"Yes, Rose," DiCaprio responded in true Jack Dawson fashion. "You're flying."
Jack and Rose, 2.0.
(E! and Saturday Night Live are part of the NBCUniversal family.)