With nearly 2 million people, Manhattan can feel pretty freakin' massive. But, in actuality, it is one teeny, tiny island. Just ask Willie Geist. 

Because, mere hours after filming his 300th (!!) episode of Sunday TODAY with Matt Damon, the TODAY veteran ran into his first ever Sunday Sitdown guest, Leslie Odom Jr. "It was a nice bit of poetry," Geist exclusively told E! News, reflecting back on when it all began. "I was just happy to get that first show on the air in April of 2016…at the height of Hamilton-mania."

Not that he ever doubted his approach to storytelling, which features hour-long interviews with stars that strive to spotlight the in depth, very real stories behind their success.

Nearly eight years in, "it means the idea for a new kind of TODAY show has resonated with our audience," he shared. "It means our amazing team of talented bookers, producers and editors has created something unique and good and compelling to our viewers."

And though he's sat down with Shonda Rhimes, Gwyneth Paltrow, Ryan Reynolds and Mila Kunis (just to name drop a few), Geist is already dreaming up his guest list for the next 300 episodes. 

"Just when I think I've been lucky enough to interview everyone on the wish list, I remember we haven't had Will Ferrell or Tina Fey or LeBron James or Jay-Z or Beyoncé or Taylor Swift or Jamie Foxx or many, many others on the show," the 48-year-old said. "There always is another big one out there."

Until the next big one lands on your screen, keep reading for a peek inside his most memorable interviews yet. And tune into Geist's 300th episode of Sunday TODAY on NBC July 16 at 8 a.m.

"There are a rare few guests who have been on twice but Ina is one of them," Geist previously told E!. "The first time, I went to her house in the Hamptons and parked in her driveway and walked in. We were both wearing denim, which I thought was a good matching look for us. We were in that big kitchen everyone knows and has seen on TV for years and years and we cooked. We sat at her table and ate lunch and then she said, ‘Let's go for a ride to the beach.'"

The Sunday TODAY host continued, "So we hopped in her Cooper with the top down. She put on a huge floppy hat and there I was riding shotgun with Ina Garten. We were driving to the beach and there was a man jogging. She honked and waved and sure enough, it was Jeffrey [Garten]. Boy, I really got the full Ina Garten experience."

"David Letterman was so cool," Geist shared. "We live 10, 15 miles away from each other and he goes to the same bait and tackle shop I go to in Westchester County, New York. We knew he liked to go fly fishing so we asked if he would come stand in a stream with me and I was surprised when he said, ‘Yes, I'll meet you in the stream. Let's go talk.'"

"We must have sat for two hours and talked and then Chip went, ‘Hey! Want to go break some stuff?' So he gave me a hammer and we had a hammer throwing contest and Joanna is standing there with her cup of coffee going, ‘God, you guys are such idiots' and she's right," he shared with a laugh. "I just love them as people. I love their show and I love what they do, but they're such genuinely good people."

"Ryan Reynolds has a line of gin called Aviation, so when we did that interview, we said let's do it in a bar," Geist shared. "So he mixed up some drinks and we talked about it. Bryan Cranston had a line of Mezcal. It feels like every celebrity has a line of booze and we're always happy to indulge and tip up a glass before we get going."

Before the pandemic, Geist would travel across the country to meet with Hollywood's biggest names. As he recalled to E! News, "You might see Al Pacino doing an interview with us that you've never seen him do before where the two of us are driving around Beverly Hills with the top down in a 1974 Cadillac."

If you ask Geist to share one of his most special interviews, it has to be his very first sit-down for Sunday TODAY with this Oscar-nominated star.  "It was the height of Hamilton-mania and the fact that we got Leslie Odom Jr. to do our first show on an unproven show will always be so meaningful to me and he will always hold a special place in my heart," he recalled, "and I'm so happy that he's gone on to such big things. I was such a fan of the show and I listened to the album all the time."

"Dolly Parton is a great hero of mine," raved Geist. "I had the opportunity to interview her a couple of times and have gone down to Dollywood and be invited again. Those are the pinch me moments. The people who you grew up loving and listening to their music and now, here you are, being invited into their world and to be able to ask them about their lives and career blows your mind."

"As a guy who grew up loving Caddy Shack and Ghostbusters, the chance to sit down with Bill Murray—a guy who doesn't do a ton of interviews—that was really special, especially when you consider he doesn't have a publicist. You just call a 1-800 message for Bill and if he wants to call you back, he will," he remembered. "He didn't actually call us back. He came into the Today show for an interview with Savannah Guthrie and while in the green room, he casually told our bookers, ‘I want to do that Willie Geist show.'"

"Time is one way to put people at ease because they don't feel pushed and stressed, but the setting is important too," Geist explained. "We interviewed Jerry Seinfeld on the stage at the Beacon Theatre—his home away from home and where he goes to do his stand up." 

(E! and NBC are both part of the NBCUniversal family.)