Lindsay Lohan (September 4, 2013)
Even Letterman's most awkward interviews can be compelling thanks to Dave's ability to ask meaningful, albeit uncomfortable questions to guarded guests. When Lindsay Lohan came on to promote Scary Movie 5, she was already far gone into her tabloid nightmare. (The actress was scheduled to start a rehab stint the following month.) The conversation is ragged and somewhat combative — Letterman tries to read her a list of jokes the staff had written about her addiction problems — but there's also a weird tenderness to their exchange. Surprisingly, the host was able to draw out the vulnerability and charm that once made her seem like the next big movie star. Viewers tuned in hoping for a train wreck; instead, they got to see one of the more tender exchanges between Lohan and a TV personality not known for pulling punches or acting paternal.