Lindsay Lohan and David Letterman phoned a mutual friend on Wednesday night's Late Show, and what followed elicited big laughs and reflective tears.
In discussing Lohan's new documentary series, Lindsay, which airs on Oprah Winfrey's network OWN, the 27-year-old actress suggested they get Lady O on the phone.
Letterman acquiesced, calling Oprah with a phony voice and pretending to be "Lindsay Lohan's secretary." The 66-year-old late-night host quickly dropped the charade, getting a laugh out of Oprah, who quipped, "Very good, Dave! The David Letterman who's retiring?"
The conversation quickly turned to Lohan, as Oprah (whom Lohan has called her "mentor") gave her take on how Lohan is doing now.
"I think she's doing really okay," Winfrey, 60, said. "I think to have cameras following you around for every phase of your life, and you are trying to pull your life together, I think that's a really difficult thing, so we're really pleased she's making some progress," Winfrey added, bringing Lohan to tears.
Letterman quipped back, "Oprah, I've spent 30 years trying to pull my life together. Where the hell have you been?"
Late Show airs weeknights at 11:35/10:35c on CBS.