While LiLo seems to struggle with the enormity of the moment, Letterman, being the master of late night, takes the reins and immediately asks Winfrey how Lohan is doing. (Winfrey has mentored Lindsay during the actress' road to sobriety, a relationship that's been heavily chronicled on the OWN docuseries Lindsay.) Lohan actually tears up at Winfrey's response: "I think she’s doing okay."
It's must-watch television, the kind Letterman has been an expert at crafting for 30 years. And, with the very recent announcement that Stephen Colbert will be replacing Letterman when he steps down in 2015, all we can say is: Good luck, Mr. Colbert. You have some very big shoes to fill.