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Adam Pally has a special knack for making hilarious-but-little-seen comedy that only gets rediscovered by a wider audience years later.

There was his beloved cult hit Happy Endings, which struggled to find viewers when it ran on ABC from 2011 to 2013 but is now finding new relevance on Netflix. There was his legendary guest-hosting train wreck on The Late Late Show that has since become an internet obsession. And now theres Champaign ILL, an alternate-universe Entourage that came and went without much fanfare when it debuted as a YouTube Original three years ago but is now making a splash on Hulu.

In this episode of The Last Laugh podcast, Pally opens up about how the gay character that launched his comedy career might look less progressive in hindsight and tells hilarious stories about the time Regis Philbin introduced him to Donald Trump, how he ended up impersonating Don Jr. on The President Show, and a lot more.

Theres so much good television. How could anyone find everything? Pally says diplomatically when I highlight his list of underappreciated credits. It would be impossible.

In Champaign ILL, Pally and comedian Sam Richardson play a pair of pathetic man-children whose lives go into a tailspin after their best friend from high schoola hugely famous rapper played by SNL alum Jay Pharoahdies tragically during a music video shoot, leaving the talentless members of his crew with nothing. Its as if Vince from Entourage was suddenly gone and Turtle and Johnny Drama were forced to survive on their own.

Entourage is a fabric of my growing up, Pally, who once hosted a 50-hour hate-watch marathon of the entire HBO series, admits. And there was something about that show that just struck a chord in me. And so we always thought, Oh, this is kind of a version of that, but if there was no money left.

When I suggest that Pally himself might have the perfect level of fame where hes not constantly harassed by paparazzi but also gets to enjoy the perks of celebrity, he replies, What are the perks you speak of? Id love to know.

There are definitely perks of fame, he admits, but hes not sure he actually gets to experience any of them. I cant call up a restaurant and be like, My name is Adam Pally, Id like a table for two. Theyd be like, Well, my name is Gary and no.

His first big break in Hollywood came in ABCs Happy Endings, which, like Champaign ILL, was created by David Caspe. Pally reveals that he and Caspe will also be collaborating on a yet-to-be-announced third series in the near future. When the show premiered, reviews repeatedly referred to his character Max Blum as progressive since, as the Advocate put it in 2011, he aggressively defies traditional stereotypes about gay men.

A decade later, Hollywood is having a larger conversation about whether straight actors should even be playing gay roles. And Pally says of course he thinks about his decision to play that character differently now.

I really loved playing that character and if they rebooted Happy Endings, I would be heartbroken if someone else was playing that character. I would be gutted, he says. But Im sure at the same time, when the character was first created, there was someone more realistically like Max who, when the part went to me, was equally gutted.

But Im sure at the same time, when the character was first created, there was someone more realistically like Max who, when the part went to me, was equally gutted.

And so I dont know what the right answer is, but I do know that we made the show with the best intent, Pally continues. Looking back on it now, Im sure there are things that we could do differently. But I am proud of that character. And I think had we got to go further, there would have been a lot more opportunities for me to play a more well-rounded version of that character. But such is life.

Despite getting cut short, Happy Endings opened a lot of doors for Pally, leading to a regular role as Dr. Peter Prentice on The Mindy Project as well as comic-relief parts in movies ranging from Iron Man 3 to Dirty Grandpa to Sonic the Hedgehog, alongside his old Upright Citizens Brigade collaborator Ben Schwartz.

Schwartz also served as his sidekick on that fateful Friday night in January 2015 when Pally got the unexpected opportunity to guest host The Late Late Show on CBS between Craig Fergusons departure and James Cordens arrival. I honestly think it was a contractual thing that was being covered up or something, Pally says of the odd circumstances that led him to host the show for one night from the CBS This Morning studio without an audience. Something wasnt right.

Pally had a feeling they were doing something special during the taping, but it wasnt until he started getting texts from his comedian friends while it was airing that night that he realized how off-the-rails brilliant it was. When a friendespecially a comedian friendtexts you, it means that something you did made an impact, he says. Because we are usually a very jealous, callous group of people. So if you get a text from a comedian friend, youre like, Oh, I think I did something good.

In the years since he deliberately bombed on late-night TV, Pally has taken on a bigger role behind the scenes, serving as an executive producer on projects like Making History, Champaign ILL anda personal favoriteThe President Show.

Pally first saw his fellow UCB alum Anthony Atamanuiks expert Trump impersonation during the 2016 campaign and he was particularly impressed with the way he could endlessly riff off-the-cuff as the candidate. It wasnt just the impression that was so good, the content was so good, he says.

When the idea of him playing Donald Trump Jr. on their Comedy Central show came up, Pally says, At first I was a little bit like, I dont know. But once he started improvising as the former presidents eldest son, it started to click. We were like, theres something here to making him a mimbo. And it worked out, it was really fun.

Listen to the episode now and subscribe to The Last Laugh on Apple Podcasts, Spotify, Google, Stitcher, Amazon Music, or wherever you get your podcasts and be the first to hear new episodes when they are released every Tuesday.

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Adam Pally on Playing Gay and Nailing Donald Trump Jr. - The Daily Beast