The thing about Letterman is that, he’s a former alcoholic. In his own way, he’s a life-long f*ck up. He managed to get the drinking under control, but obviously, the philandering and other self-destructive behavior has continued to bite him in the ass throughout his career. What it does is to make him a more empathetic interviewer with someone like Lindsay Lohan, who — for reasons it’s hard to make sense of — he and Tina Fey and Lorne Michaels and a few others continue to pull for.
There are a number of jokes made in the interview, and a few funny moments, but in the end, I honestly think there was some sincerity on both Letterman and Lohan’s part. He badgered her about rehab; she took it in stride, and they came to a happy place where Lohan could — once again — dedicate herself to getting her sh*t together.
It’s great television, really. I don’t know if it’ll mean a damn thing in three days, but for 15 minutes, you get the feeling that there might be a future for Lohan.