Lindsay Lohan, Oprah, David Letterman: Comedy dream team. Who knew?

April 10, 2014

Lindsay and Dave give Oprah a call. (Jeffrey R. Staab/CBS)

Guess who has surprisingly impressive comedic chemistry? Lindsay Lohan, Oprah and David Letterman — the comedy dream team you never knew you wanted until you saw them all together.

Okay, technically they weren’t all physically in the same room: Lohan was a guest on “The Late Show” Wednesday night to promote her disturbing reality series “Lindsay” on the Oprah Winfrey Network and upcoming guest spot on CBS comedy”2 Broke Girls.” During Lohan’s interview, she and Letterman made a “totally spontaneous!” phone call to Oprah that resulted in a highly entertaining few minutes and illustrated another reason why it’s a shame Letterman is retiring soon.

The three have so much history through their own separate storylines, which only added to the spectacle. Oprah and Letterman are enemies-turned-pals. Letterman is the only talk show host that Lohan seems to genuinely enjoy, and the admiration (surprisingly) has always appeared mutual. Oprah has adopted Lohan as her new pet project, trying to help get her life together and and giving her a reality show. Lohan looks to be tolerating Oprah given that the show, despite terrible ratings, has gotten her name back in the spotlight.

Anyway, Wednesday’s three-way call resulted in a confused Oprah attempting to play along off-camera; a grumbling Letterman trying to cover for how much he seemed to enjoy the interaction; and a cackling Lohan who treated the whole thing like Dave and Oprah were her parents who were being so embarrassing, but was secretly delighted to be in the middle of it all.

“How’s Oprah, you never see Oprah, right?” Letterman kicked things off.

“Never see her, only when we’re on [camera],” Lohan said convincingly, then switched gears to gushing. “No, actually she’s become a guiding light to me. She’s been an amazing human being to me in my life and it’s helped…She’s become a mentor to me and I allow it now.”

“Isn’t it fascinating that here’s a woman — ” Letterman started, as Lohan suddenly pulled out her iPhone. “What are you doing?” he asked.

“I think that maybe I should just call her right now. Should we call Oprah?” Lohan asked.

“Now, we’re  not,” Letterman said as the audience started wildly applauding.

“I think so. Is there a phone? Have you got a phone?” Lohan urged.

This went on back and forth for awhile, Lohan leading the audience along with an “O-prah! O-prah! O-prah!” chant.

“She’ll just want to show up and take over the show now,” Letterman complained. “Now I’ve tried to call Oprah on the phone before and I cannot get through to her.”

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“Okay, well, I think I might be able to,” Lohan argued.

“You can’t get through to Oprah,” Letterman scoffed. Finally, he “agreed” to it, pulling out a giant touch-tone phone behind his desk and instructed Lohan to write the number on a piece of paper so he could dial. “Now do you have something to say to Oprah? Because I get nervous around Oprah.”

“Can’t even use an iPhone,” Lohan guffawed as she wrote the number down, hiding it from the camera. “Don’t take a shot of this number, or I’ll never work again.” (That likely wasn’t a joke.)

Letterman dialed the phone, and all of a sudden the Voice of Oprah came in over the studio speakers: “Hello?”

“Could I speak to Oprah Winfrey, please” squeaked Letterman, using a fake voice.

“Uh, this is Oprah,” she replied.

“Hi, this is Lindsay Lohan’s secretary,” Letterman said, raising his voice even more.

“Who is this?” Winfrey asked, sounding genuinely annoyed.

Letterman returned to his regular voice. “It’s Dave, Oprah, it’s Dave.”

“Oh my God,” Winfrey laughed, sounding not-all-that-amused. No one messes with Oprah.

“Sorry,” Lindsay said gleefully taking the phone.

Letterman mumbled something about Oprah being “pissed off.” “How are ya?” he asked.

“Very good, Dave!” Oprah said brightly. “The David Letterman who’s retiring?”

“All right that’s right,” Dave Letterman faux-grumbled. “How’s our friend Lindsay doing?”

“I think she’s doing okay. What do you think?” Oprah asked.

“I’ve loved her since she was six years old,” Letterman said.

“You must really be loving her now!” Oprah laughed for an awkward beat too long before getting in Serious Mode. “No, I think she’s doing really okay. I think to have cameras following you around for every phase of your life, and you’re trying to pull your life together, I think that’s a really difficult thing. So, yeah, we’re really pleased that she’s making some progress.” The camera zoomed in on Lohan’s face, who started to tear up.

“Oprah, I’ve spent 30 years trying to pull my life together, where the hell have you been?” Letterman asked.

Lots of laughter and applause from the crowd. Oprah told Dave that he should be doing fine because he uses the same meditation teacher (“Meditation Bob”) that she and Lohan also visit.

“You know what else, Oprah, that I’ve switched to now, that is really fantastic? Scientology,” Letterman said to much laughter.

“Oh goodness gracious, let’s go back to meditation,” Lohan said. (Boy, what we wouldn’t give to hear Meditation Bob’s stories.)

“Oprah, when are you coming on the show?” Letterman asked. “I’m sorry, I’m using your time to book Oprah,” he said to Lohan.

“Yeah exactly, I feel like I’ve just been pawned off,” Lohan laughed.

Oprah demanded to know what Letterman and Lohan could be talking about. Letterman started to explain a complicated inside joke about scrambled eggs that had been the topic of conversation a few minutes earlier.

“Now Oprah, listen to me, this show, the Lindsay Lohan show, it should start every day with breakfast,” Letterman suggested. “Can you do that?”

Oprah agreed it was possible. “I’ve never seen Lindsay eat breakfast, but doesn’t she eat well on camera?” Oprah mused. “Every time we follow her to a restaurant…”

“This conversation!” Lohan groaned in faux-mortification, loving being in the center of attention.

Finally, after some more banter about Letterman being a spiritual guru, they started wrapping things up. “Dave, listen, I gotta come on the show before you leave,” Oprah said.

“Oprah, I want you to come on the show,” Letterman started. Lohan waved to get his attention. “We should come together! We should come on together,” she whispered loudly.

“What? You and Oprah?” Letterman asked dryly before turning back to the phone and rolled his eyes, saying, “Yeah here’s an idea, Oprah…”

The audience cracked up; and a comedy dream team was born.

Emily Yahr covers pop culture and entertainment for the Post. Follow her on Twitter @EmilyYahr.
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