"There's no question that this is a monumental and historic moment," McHale tells PEOPLE

By Patrick Gomez
Updated July 08, 2015 04:25 PM
Credit: Scott Clarke/ESPN Images; Josiah Kamau/BuzzFoto/Getty

Joel McHale is known for his biting jokes, but when it comes to Caitlyn Jenner receiving ESPN’s Arthur Ashe Courage Award at the upcoming ESPYs, the funnyman isn’t laughing.

“There’s no question that this is a monumental and historic moment. I mean, she’s the first,” the ESPYs host, 43, tells PEOPLE of Jenner. “To [transition from male to female] is courageous and difficult. I can’t imagine that it was an easy decision or process.”

McHale is well aware that some have been critical of the decision to award Jenner, but the Community star says there is “no question” that the Olympic gold-medalist is deserving of the recognition.

Jenner “was the biggest athlete next to Muhammad Ali” and “completed an incredible feat,” McHale says of Jenner’s Olympic decathlon win in 1976.

But just because McHale is happy to honor Jenner doesn’t mean The Soup host’s signature sense of humor will not be on full display – especially if the Kardashians show up.

“If you’re sitting there and you’re super-famous, I’ll probably be mentioning you,” McHale says of his plan to “equally spread out” his roasting of the attendees.

Even so, the former White House Correspondents’ Dinner host has already conceded that there is no way he’ll make every sports fan happy with his jokes.

“It’s a no-win situation for jokes, because the minute you start making fun of somebody’s team, they hate you. And if you make fun of someone’s rival, they love you,” says McHale. “It’s like being at the Correspondents’ Dinner. The Democrats are not going to laugh at the jokes that are about them, and vice versa with Republicans … I’ve made a career out of upsetting people.”

The ESPY Awards will air Wednesday, July 15, at 8 p.m. on ABC.