Letterman Grilled Lindsay Lohan Last Night, Made Her Cry

Is it cool to say that Lindsay Lohan earned some of my respect last night? Probably not, but I think she did. As much I might want to bag on her right now, the fact is that it had to be hard to sit in a chair next to Letterman — who has rightfully cracked hundreds of jokes at her expense over the years and held nothing back last night — and endure what she endured, most of the time rather graciously and with a smile on her face, until, that is, the end, when she finally began to break down a little after Letterman praised her for having “enough spine, enough sense of yourself, enough poise to come out here and talk to me.” Frankly, watching a broken person squirm on stage under the bright lights made me kind of sad.

Lohan, who’s set to soon report to a court-ordered rehab stint, made some jokes at her own expense, telling Letterman that she considered coming out in a dress that still had a price tag attached to it, in reference to her proclivity for stealing things. I couldn’t tell if that showed self-awareness on her part or if it was a denial mechanism.

The most awkward part of the interview, unquestionably, came when Letterman grilled her about her upcoming rehab stint.

“How many times have you been in rehab?” Letterman asked. “Several,” Lohan replied.

“And how will this time be different? What are they rehabbing, first of all? What is on their list? What are they going to work on when you walk through the door?” Letterman countered.

“We didn’t discuss this in the pre-interview, I’m just saying to everyone,” Lohan replied.

I defy you to watch the interview for yourself and not cringe.