Dave's Faves: Top 10 Repeat Guests on Letterman

From flirty Julia Roberts to flighty Regis Philbin, these stars kept coming back for more

4. Howard Stern

No wonder David Letterman and Howard Stern saw each other as kindred spirits. Both proudly idiosyncratic, both refusing to kowtow to corporate bosses, they were two peas in a grouchy pod. What made Stern's appearances great in the Late Night days was that his button-pushing provocations helped give Dave's show its edge. (In 1984, Stern wondered how Vice President George H.W. Bush could get aroused being married to the much-older-looking Barbara Bush.) Few stars stood up for Letterman as defiantly as Stern did during the late-night wars, and even though the two men had a falling out later, they renewed their friendship before Dave's retirement. Those final Late Show appearances allowed viewers to enjoy some in-depth interviews and be reminded how good both men were in drawing out their guests through interesting, engaged conversation.

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