‘SNL’ boss Lorne Michaels faces his toughest challenge yet with 50th season

As ‘Saturday Night Live’ prepares to celebrate its 50th anniversary, legendary show boss Lorne Michaels is also preparing for his “toughest” season to date.

“It’s hard to imagine a scenario for the show where the stakes could be any higher,” said James Andrew Miller, who wrote the book, “Live from New York: An Uncensored History of Saturday Night Live”,

“It’s the ultimate SNL trifecta,” he told Page Six, “A Presidential election year which is historically the deep end of the SNL pool; a year when all eyes will be on Lorne to see whether or not it will be his last, at least in terms of full time presence; and the show’s 50th anniversary, taking place in a bitterly divisive time for this country.”

Hillary Clinton (right) played a bartender opposite Kate McKinnon — playing Clinton — in a skit in October 2015. NBCU Photo Bank/NBCUniversal via Getty Images

Inside the hallowed hallways of studio 8H at Rockefeller Center, where ‘SNL’ has broadcast live at 11:30 p.m. ever since its first episode on October 11, 1975, Michaels and his staff are readying for the clash between Donald Trump and Kamala Harris, which is just 44 days away.

From Trump hosting – twice – to his one-time rival Hillary Clinton playing a world weary bartender and Tina Fey’s infamous depiction of former VP candidate Sarah “I can see Russia from my house” Palin, the show has always poked fun at politics.

Indeed, we now face the prospect of Trump and Harris making an appearance as the battle heats up, despite the fact a highly-placed Hollywood insider argued that “SNL” is now constrained by fears of being “cancelled.” (Page Six has reached out to “SNL” for comment.)

Maya Rudolph will return to play Democratic candidate Kamala Harris in this 50th season of “SNL.” NBCU Photo Bank via Getty Images

 Back in 2020, Michaels, who turns 80 in November, announced he planned to retire after the 50th season sparking succession rumors, with runners and riders from Fey to Seth Meyers. But this week he hedged on his plans.

“As long as it’s important and I can be useful, I’ll stay,” he told The Hollywood Reporter.

Larry Sanders (right) — who played Presidential candidate Bernie Sanders in the show — starred opposite the real Sanders (left) in February 2016. NBCU Photo Bank/NBCUniversal via Getty Images

Next month, Jason Reitman, who as the son of “Ghostbusters” director Ivan Reitman grew up surrounded by “SNL” legends, including Dan Aykroyd, will debut his much-anticipated movie, “Saturday Night”,  his reimagining of SNL’s chaotic first episode.

Michaels, friends tell The Post, will likely not see the film – he has lived it.

The industry vet, who introduced the world to stars including Eddie Murphy, Bill Murphy to Gilda Radner, Kristin Wiig, Adam Sandler and Will Ferrell, has certainly pulled out the big guns for the first five episodes of the new season.

Freshly crowned Emmy-winner Jean Smart, of “Hacks” fame will join musical guest Jelly Roll for the premiere on Saturday, followed by Nate Bargatze with musical guest Coldplay, Ariana Grande with musical guest Stevie Nicks and Michael Keaton with musical guest Billie Eilish.

Former NY Mayor Rudy Giuliani (center) appeared on “SNL” on “Weekend Update” with Tina Fey and Jimmy Fallon in December 2001. NBCUniversal via Getty Images

Former “SNL” scribe John Mulaney will helm the last episode before the election on November 2 with musical guest Chappell Roan.

It was actually Michaels who wanted Roan, the chart topper behind hits “Pink Pony Club” and “Hot To Go,” sources said.

“Lorne always has his finger on the pulse,” an insider noted.

But, it takes more than big stars for the show to be funny and capture the zeitgeist.

“At the end of the day, what’s going to matter most is the material,” said Miller.

The late Arizona Senator John McCain and Fey, playing his VP pick, Governor Sarah Palin, on “SNL” in October 2008. NBCUniversal via Getty Images

“The country is not in a laughing mood. Kamala may be smiling, but few regard this as a fun election. So how does SNL thrive in such a politically divisive climate? They don’t want to be part of the political conversation; they want to lead it.”

He continued,”Over the course of 50 years, there have been times when the show has been regarded as politically agnostic; liberal; and even conservative, but given the bitterness, fear, and historic hatred out there, this may be SNL’s toughest balancing act in its history.”

The show’s stars were less than thrilled when Trump hosted as a Presidential candidate in 2015, with protestors flocking outside 30 Rock. 

Ex cast-member Taran Killan — who insiders say could return to play VP candidate Tim Walz after Steve Martin turned down the gig — told NPR in 2017, “It was rough … It was not enjoyable at the time and something that only grows more embarrassing and shameful as time goes on.”

David (from left) as Bernie Sanders, Woody Harrelson as Joe Biden, and Rudolph as Kamala Harris during the “DNC Town Hall” sketch on Saturday, September 28, 2019. NBCU Photo Bank/NBCUniversal via Getty Images

Trump himself has blasted that the show should be “put out to rest”, and when asked whether he would accept an invitation to return, his rep did not respond.

“I don’t think the cast or writers would be thrilled,” a senior TV industry source told Page Six of the former President potentially coming on the show.

And, as Miller said, it would be difficult to say the least to have either candidate on the show.

“If Harris and or Trump do agree to do the show, writing that sketch is going to have the highest degree of difficulty. It has to earn the approval of the candidate and Lorne, and it better be funny. Again, not something that was prohibitive in the past, but crazy challenging in this climate,” he said.

Tiffany Haddish surprised Colin Jost and Michael Che on “Weekend Update” in November 2017. Industry insiders say the duo are the only ones who can get away with non-woke comedy on the show. NBCU Photo Bank/NBCUniversal via Getty Images

A leading political PR, who has worked extensively on election campaigns, told us, “I think “SNL”s viral moments help bring the election to a wider audience, like Larry David playing Bernie Sanders.

“While it would be funny (to see Kamala on the show), ‘SNL’ is a hard thing to do. It has to be the right sketch, and I think it could only highlight the fact that she’s not been giving interviews.” 

Trump has been played by Alec Baldwin and most recently, James Austin Johnson.

Alec Baldwin as a rambunctious Donald Trump in October 2017. NBCU Photo Bank/NBCUniversal via Getty Images James Austin Johnson has played Trump for the past few seasons. Will Heath/NBC via Getty Images

Michaels revealed that Trump will be revamped this season — dodging the question of whether Johnson will reprise his role.

“Trump has morphed. James, who I think is brilliant, played Trump as the sort of diminished Trump. The guy at the back of the hardware store holding court, and that played because it felt relevant,” Michaels told THR, “But we are going to have to reinvent it again because, well, you saw the debate.”

Harris, meanwhile, will be played again on “SNL” by another former cast member, Maya Rudolph.

Baldwin and Rudolph play Harris and Trump during the “Dueling Town Halls” Cold Open on Saturday, October 17, 2020. NBCU Photo Bank via Getty Images Fey has been rumored to be a top contender to replace Michaels. But friends think she would not take the gig. WireImage Will Ferrell — seen with Cher Oteri on air in 1995 — is one of the show’s biggest breakout stars. NBCU Photo Bank/NBCUniversal via Getty Images “SNL” debuted on October 11, 1975 and made stars out of the cast — Chevy Chase (from left), John Belushi, Laraine Newman, Gilda Radner, Garrett Morris, Jane Curtin and Dan Aykroyd, ©NBC/Courtesy Everett Collection

There have been moments over the past few years where some of the new bright stars have made their political and lifestyle views clear.

Bowen Yang, one of the biggest stars to debut over the past few years, admired recently he did not want to be the “woke scold”, telling the New Yorker, “It’s taught me about my place on the show being kind of strange and unique.

“I never expected to be a Nora Dunn being furious that an Andrew Dice Clay is there,” he said.

Chase and Radner — playing Emily Litella — on “Weekend Update” during Season 1 in 1975. ©NBC/Courtesy Everett Collection

However, the Hollywood insider insisted, “It’s also very hard to do comedy with the rules of comedy now, you can’t get away with what you could do 15 to 20 years ago, it’s all too serious — except for Jost and Che, they seem to get away with everything!

“It’s not as exciting, as edgy and creative and that’s only because everybody is just afraid. Lorne would argue, ‘no, we take our shots’, but not really, because you’re afraid you’ll be cancelled.”

For its anniversary, “SNL” will be celebrated with a star-studded event at Radio City Music Hall in February followed by a reunion episode that same month featuring a who’s who of “SNL’s” past.

Eddie Murphy (far left) was a breakout star on “SNL” in 1981. Corbis/VCG via Getty Images

A show insider said, “There is a lot of excitement, everyone is so happy to be back, the lineup is awesome and the focus is the political season.”

As for Michaels, he admitted that he may have to rely on colleagues moving forward, but insisted the show can count on him for the immediate future,

“It’s more about keeping it on course than anything else, and, obviously, I really love it,” he told THR. 

Jason Reitman’s movie, “Saturday Night,” follows the chaotic first episode of “SNL”. ©Sony Pictures/Courtesy Everett Collection

“And every year there are more and more people whom I rely on for other things, but, in the end, you really need someone to say, ‘This is what we’re doing.’ So, I don’t really have an answer; I just know that this is kind of what I do and as long as I can keep doing it, I’ll keep doing it. There’s no immediate plan.”

“He and SNL will always be inextricably linked,” said Miller. “When Lorne does leave, there’s no reason to put everything that he does into the hands of just one person, and every reason to split the many responsibilities between several individuals. It would be unfair to expect one person to replace him. There’s not another Lorne out there.”