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Renowned actor, filmmaker, and Hollywood heartthrob also opens up about his new project, “The Midnight Sky”

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Celebrated actor, filmmaker, and humanitarian George Clooney made his long-awaited Stern Show return on Wednesday, sitting down with Howard for the first time in over two decades. He opened up about a range of subjects, including his new Netflix movie “The Midnight Sky,” the ups and downs of his storied career, and the great love story he and his wife Amal Clooney have shared, but George kicked off his conversation by joking with Howard and co-host Robin Quivers about how he hoped to soon win his third “Sexiest Man Alive” award.

“I’m running a fairly strong campaign this year,” the Hollywood star said with a laugh.

Always the jokester, Clooney has been known to prank his celebrity friends and co-stars on many occasions. In one, he repeatedly took out full-page “For Your Consideration” ads featuring Matt Damon in a green speedo in the hopes of helping him win his own “Sexiest Man Alive” award. “We kept pummeling him for, I don’t know, two years—and they finally gave it to him,” George said.

In another, he left his friend and short-lived roommate—actor and comedian Richard Kind—an unlikely present in his cat’s litter box. One of the most “brutal” stunts he pulled was on mega-star Brad Pitt, who found himself in George’s sights after pulling off a practical joke of his own while the two shot their caper sequel “Oceans Twelve” in Italy. He’d put up posters all around town saying Clooney demanded his fans in Italy call him Danny Ocean, the character from the films. “It got in the papers,” Clooney said, explaining the locals took it seriously and the stunt even made the paper. “I thought they were nuts … as if Danny Ocean is a character you really need to get into.”

George didn’t wait long before settling the score. For starters, he tagged Brad’s Toyota Prius with a marijuana leaf-shaped bumper sticker which read “Fuck Cops.” It didn’t take long for a police officer to pull him over. He also acquired some Brad Pitt-adorned stationary from Jimmy Kimmel and used it to write several letters while impersonating Brad. In one, he asked a voice coach to help his good friend Meryl Streep pull off a British accent. The coach eventually sent George a giant folder filled with coaching CDs which he then used to prank the acclaimed actress.

“I sent that thing of voices to her, the greatest actress of all time … and I sent it from Brad with a card that said ‘Dear Meryl, I hear you’re going to play the Iron lady. This guy helped me with my accent in “Troy,”’” George said, saying he kept the prank a secret from her until seeing her years later at John Krasinski and Emily Blunt’s wedding.

Howard was in disbelief. “I’m afraid of you,” he joked.

“Well, he started it,” George laughed.

In addition to directing and starring in some of Hollywood’s biggest blockbusters, George has gained a reputation over the years for his activism, humanitarian work, and philanthropy. In one famed example he recounted for Howard, Clooney generously gifted 14 of his best friends $1,000,000 each — in cash.

“At the time I was a single guy and I was making out my will. I knew who I was going to leave it to—it was these guys, I slept on their couches and they loaned me money,” George told Howard. “I was making this will out and I was like, ‘What the fuck are we waiting for? For us to be gumming our bread?”

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“It felt like, let’s just get the will part over with while we’re still around,” he continued.

Considering George’s passion for benevolence, it’s unsurprising that when the longtime Hollywood bachelor finally did settle down it was with the distinguished international human rights lawyer Amal Alamuddin. The high-powered duo’s relationship has generated headlines since the very beginning, but on Wednesday George offered new details of how their love first blossomed.

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“It’s a great story, actually,” he said, explaining the two first met when a mutual friend brought her over to his place in Lake Como, Italy. “In walks Amal and she’s, you know, stunning and funny and the smartest person in every room she walks into—and I was really taken with her.”

He told Howard the two took things slow at first, foregoing romantic overtures for a cordial long-distance friendship. “I liked her but … I couldn’t tell if she liked me. I’m 17 years older than her, so she might’ve thought I was grandpa,” he laughed.

George finally made his move after inviting her to watch his film get scored at one of London’s legendary recording studios. “I thought, ‘If you’re ever going to impress anybody it’s with a 150-piece orchestra at Abbey Road,’” he laughed.

“She’s gotta be impressed,” Howard said.

George wasn’t so sure considering all the humanitarian crises she’d been dealing with that day. “We went out to dinner quietly—no one saw us. It became romantic pretty quickly,” he said. “Once I knew she was interested, then I think we were together from that moment on.”

“It was really interesting because we had to hide for a couple months,” he continued. “You want to get to know each other and spend time with each other and not do it on the front page of Hello! magazine.”

The two were on a safari in Africa not long after when he realized Amal was the woman he wanted to marry. He put an elaborate proposal plan in motion soon thereafter which involved a homecooked, candlelit dinner, a custom engagement ring, and a romantic record recorded by his famed aunt Rosemary Clooney.

“I got it all timed out so I’m going to ask her on this one song. We’ve never talked about marriage, so I don’t know what’s going to happen,” he said, explaining he hid the ring in a drawer behind her and told her to dig through it for something to light the candles. “She opens the drawer and there’s a ring in it, and she looks and goes … ‘There’s a ring.’ Like, somebody else had left a ring there 10 years ago.”

George told Howard he got down on one knee and stayed there for quite some time as Amal was in such shock it took her 20 minutes to formulate a response. “Finally, I said to her, ‘Look, I just need a yes or a no because I’m 50-something and my hip can go out.’”

She eventually said yes, of course, and the two were married one year to the date after he bequeathed his friends their cool million. “Maybe it was karma,” George said.

Rosemary isn’t George’s only famous relative, either. His cousin Miguel Ferrer starred in “RoboCop” and on “Twin Peaks,” his uncle José Ferrer made history as the first Hispanic actor to win an Oscar (for 1950’s “Cyrano de Bergerac”), and his father Nick Clooney was a longtime journalist and TV host.

“We were a show business family,” George explained at one point.

Considering fame runs in the Clooney’s blood, it’s perhaps surprising George’s father originally cautioned him against becoming an actor. “He said the odds of you succeeding in this industry are virtually none and it’s a dumb thing to do,” George recounted. “He was completely right about it, and it required a lot of luck on my part.”

Luck may have been on his side, but Clooney still needed to overcome several early career struggles before making it big. He starred on several failed pilots and short-lived TV shows, including “Sunset Beat,” which saw him playing an undercover cop by day turned rock star by night. It was around that time he also moonlighted as a women’s shoes salesman, and it’s not a job he looks back on fondly.

“I had to spread blue powder on their corn and then put the shoe on,” he recalled, saying the horrible memories of those days always kept him grateful for any acting work he later got. “When I’m sandpapering my Bat-nipples off, I’m still going, ‘I’m good, man.’”

His other early TV roles included guest stints on hit sitcoms like “Golden Girls,” “The Facts of Life,” and “Roseanne” as well as a turn in the low-budget cult film “Return of the Killer Tomatoes!” But Clooney’s career trajectory changed permanently after he was cast as Dr. Ross on the smash-hit hospital drama “ER.”

“I always felt like I was a journeyman actor, just plugging away—hopefully I’ll get some good roles as I go. It was late, I was 35 when it hit,” he said.

Suddenly, George was a household name. Even at 35, George had plenty to learn. He told Howard he picked up a great acting tip from legendary filmmaker Steven Spielberg, who showed up on set during “ER’s” first season.

“He came over and goes let me show you something. He walked me back to the monitor and did a playback and said, ‘If you hold your head still, you’ll be a movie star,” George recalled, adding, “I think I was doing too much moving around.”

Clooney’s career skyrocketed but not every one of his projects from that era was an overwhelming success. Some, like “Three Kings,” “Out of Sight,” and “O Brother, Where Art Thou?,” underperformed at the box office despite being films George remains proud of.

George shared several anecdotes about filming “O Brother,” a Southern-set take on Homer’s epic poem “The Odyssey.” He told Howard the critically adored Coen Brothers movie got an unexpected script punch-up from one of George’s relatives, who lived in rural Kentucky.

“I sent a tape recorder to my Uncle Jack and I said read the whole script into this tape recorder and I’ll get you a dialect coach [credit] in the film,” he recalled. “I get the tape back and I play it and I hear, ‘George, I don’t think folks around here talk quite like this here, but we’ll give ‘er a go!’”

George has less fond memories of his turn as the Dark Knight in Joel Schumacher’s much maligned 1997 box-office bomb “Batman & Robin.” In fact, his experience was so bad he later cautioned his friend Ben Affleck against taking up the cape and cowl himself.

“Ben didn’t listen to me and he ended up doing a great job, and I was wrong,” he said, adding, “I said don’t have nipples on the suit.”

“Will you ever revisit that movie?” Howard asked.

“No,” George said. “It’s so bad that it actually hurts to watch, physically. You’ll be flipping channels and it’ll just pop up and I’m like, ‘Oh, no, no, no.”

If given another opportunity, Howard wondered if his guest would’ve approached the part from a different angle.

“I couldn’t have done that one differently. It’s a big machine, that thing. At that point, I was an actor getting an acting job,” he said.

“The truth of the matter is: I was bad in it,” he added, explaining the script, performances, and direction were all bad despite there being such a talented cast and crew. “We all whiffed on that one,” he concluded.

If there’s one action-movie character even more storied than Batman it’s super spy James Bond, but George assured Howard that’s not a role he’d be interested in playing.

“I’m too old, man,” he said.

However, he did offer up a suggestion for who might follow in Sean Connery, Timothy Dalton, and Daniel Craig’s vaunted footsteps — Idris Elba.

“It’s just stupid they haven’t done it yet. Honest to God,” Clooney said. “Why not Idris? It would be fantastic and it would say so much about the industry as well, and he would be off-the-charts great in it.”

Just because George doesn’t want to play 007 on the big screen doesn’t mean he’s afraid of a little adventure. He used to speed through life on a motorcycle until a near-fatal 2018 accident made his life flash before his eyes.

“I got in a motorcycle accident, so I’m off of motorcycles now,” he recounted for Howard. “A guy turned in front of me and I was launched … It knocked me out of my shoes. My shoes were all the way down the street. I hit his windshield with my helmet.” There was screaming, glass in his mouth, and plenty of blood.

“I’ve been riding for 40 years. You know when you do that, you’re toast … [but] I landed on my hands and knees … If I’d landed any other way it probably would’ve killed me. I used up my nine lives on that one,” he continued. “I was in the hospital and Amal came and got me—in a very vulnerable position, I would say—and said, ‘Okay, that’s it with motorcycles.”

Even so, an actor’s life can still contain unforeseen dangers. George’s award-winning performance in “Syriana,” for example, left him with more than just an Oscar statute. He told Howard an on-set mishap left him with a debilitatingly painful spine injury which took him years to overcome.

“I tore my [spine] in two places … all the spinal fluid goes out and your brain sinks in your head,” he said. “It’s really, unbearably painful. You have to lay down and you can’t get up—I thought I had a stroke. When I finally got to a doctor … I had spinful fluid coming out my nose.”

“I did a 12-hour surgery on Christmas Eve,” Clooney continued. “You always worry about the doctor you get on Christmas Eve,” he added with a laugh.

The pain was so bad there were times George thought he couldn’t possibly survive. They prescribed him plenty of painkillers, but he said taking them was a slippery slope and he eventually flushed them all down the toilet. He eventually found better results with a pain management guru who helped George approach the problem a little differently.

“His idea was that you have to rethink pain … in the sense that if you were born feeling the way you are right now, you wouldn’t know you were in pain,” George explained. “In a way, the pain you’re experiencing is mourning for the way you used to feel.”

In another death-defying story, Clooney recounted getting carjacked at gunpoint in South Sudan.

“I’d been reading all these Nicholas Kristof articles about what was going on in Darfur. There were no news sites that were running it,” he said. “There were 300,000 people murdered there, millions displaced, and there was no story, so I thought let’s go there and at least make it louder.”

“We got pulled over by these kids … They just wanted the truck … and they pulled us out and stuck a gun to our chest,” he recalled. One of his traveling companions eventually diffused the situation, but not before giving George a scare. “In the middle of nowhere, it was concerning. I thought we were in trouble,” he added.

George has throttled back on his international adventures since getting married and having children, but he hasn’t completely stopped putting himself in peril. He told Howard how shooting “The Midnight Sky” on location in Iceland was so grueling it sometimes led to his eyelids freezing together during takes.

For one of his next films, Clooney plans to adapt John Grisham’s baseball-themed novel “Calico Joe.” It was Bob Dylan who brought him the idea. On Wednesday, he confessed he climbed aboard the project before even reading the book. “I don’t give a shit. ‘Blood on the Tracks,’ man. I want to be in that room,” he laughed.

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Hollywood, like most other industries, went into disarray after the onset of COVID-19. While films are once again resuming production, shooting schedules and release dates are anything but set. George opened up to Howard about how the quarantine has affected not only his career but also his life at home. Suddenly he finds himself cooking, cleaning, and doing more laundry than he’s done in decades. Before signing off for the morning, George also offered everyone a message of hope.

“We should all remember we’re going to get through this. It’s been a shit year and we’re gonna get through it. These vaccines are going to take hold,” Clooney assured Howard, co-host Robin Quivers, and their listeners. “Hang in there, we’ve got a couple more months to get through it. Don’t bail on it now, we’re going to all get through this thing together, and put on a fucking mask.”

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“The Midnight Sky” debuts Wednesday, Dec. 23 on Netflix.