Holly Hester the Boss
Holly Hester enjoys one of David Letterman's trademark cigars and sits at his desk. These two supposedly dated for a year way back when.

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Holly Hester Biography

The Other Intern
Holly Hester was David Letterman's girlfriend for awhile in the 1990s. Holly Hester is one of two women (along with Stephanie Birkitt)... More »
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Holly Hester