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Watch David Letterman Grilling Politicians And Pundits Through The Years

David Letterman Grilling Politicians And Pundits Through The Years
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Associate Politics Video Editor, The Huffington Post

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Reporter, HuffPost

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WASHINGTON -- In the weeks leading up to Wednesday's final show, David Letterman has been hailed as a comic genius, a revolutionary who stormed the networks in a Velcro suit. It’s hard to overstate his influence on comedy in general, and on every talk show host that has followed since. He may be leaving the airwaves, but the late night landscape is full of people who have been influenced by Letterman.

When he's gone, one thing that we may not actually see again on mainstream television is Letterman's unique, prickly interview style. The comedian could provoke intense, passionate, and even -- dare we say it -- real exchanges with his guests.

"Once he retires, there's nobody left to be scared of," Tina Fey recently told Rolling Stone. "It's all friendliness now."

Sure, there was the celebrated awkward moment with Cher, a recent gruesome exchange with a clueless Dan Patrick and a teary moment with Lindsay Lohan. But Letterman was toughest on those who deserved it -- the politicians, pundits and presidential candidates who stopped by to plug themselves.

After Sen. John McCain (R-Ariz.) stood him up (and lied about the reason) during his 2008 presidential campaign, Letterman turned the incident into a running gag. It’s hard to imagine Jimmy Fallon inserting himself into a presidential race.

Watching these interviews now, you get the sense that so many politicians underestimated Letterman. They showed up expecting a bunch of softball questions, a chance to tell a few jokes and spin a few humanizing tales. Instead: Hillary Clinton is asked about her husband’s infidelity, Sen. Rand Paul (R-Ky.) gets schooled on school funding and Bill O’Reilly is grilled on the Iraq War.

By the end of a Letterman comeback quip or rebuke, you can see the look of defeat (or mild nausea?) on their faces. And you can see the comedian cared about a lot more than top 10 lists.

Watch the video above for a small fraction of Letterman’s riveting exchanges with politicians and pundits.

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Before You Go

David Letterman's 'Late Show'
Bill Murray Spray Paints Dave's Desk(01 of17)
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Bill Murray spray paints Dave's desk on the first taping of "The Late Show with David Letterman" August 30, 1993 on the CBS Television Network. Photo: Alan Singer/CBS ©1993 CBS Broadcasting Inc. (credit:CBS)
Dennis Rodman Gives Letterman A 'Rodman'(02 of17)
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Dennis Rodman gives Dave a new look on "The Late Show with David Letterman," August 20, 1996 on the CBS Television Network. Photo: Alan Singer/CBS ©1996 CBS Broadcasting Inc. (credit:CBS)
Robin Williams And His Glorious 'Stache(03 of17)
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Robin Williams on the second taping of "The Late Show with David Letterman," August 31, 1993 on the CBS Television Network. Photo: Alan Singer/CBS ©1993 CBS Broadcasting Inc. (credit:CBS)
Demi Moore Shows Off Her 'G.I. Jane' Skills(04 of17)
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Demi Moore on "The Late Show with David Letterman," July 2, 1996 on the CBS Television Network. Photo: Alan Singer/CBS ©1996 CBS Broadcasting. (credit:CBS)
Howard Stern -- Is That You?!(05 of17)
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Howard Stern in full drag on "The Late Show with David Letterman," December 20, 1995 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. Photo: Alan Singer/CBS ©1995 CBS Broadcasting Inc. (credit:CBS)
A Young Chris Rock(06 of17)
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Chris Rock performs stand-up on "The Late Show with David Letterman," June 13, 1994 on the CBS Television Network. Photo: Alan Singer/CBS ©1994 CBS Broadcasting Inc. (credit:CBS)
Paging Dr. Ross(07 of17)
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Actor George Clooney on "The Late Show with David Letterman," November 23, 1995 on the CBS Television Network. Photo: Alan Singer/CBS ©1995 CBS Broadcasting Inc. (credit:CBS)
Sean Connery's Bond-Level Entrance(08 of17)
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Sean Connery enters the stage via Jet Pack on "The Late Show with David Letterman," October 25, 1993 on the CBS Television Network. Photo: Alan Singer/CBS ©1993 CBS Broadcasting Inc. (credit:CBS)
There's Nothing More '90s Than 'Seinfeld' & 'X-Files'(09 of17)
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Jerry Seinfeld and David Duchovny from the "X-Files" on "The Late Show with David Letterman," November 10, 1995 on the CBS Television Network. Photo: Tony Esparza/CBS ©1995 CBS Broadcasting Inc. (credit:CBS)
Dave Learns A Thing Or Two From Kid Scientists(10 of17)
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Kid Scientists on "The Late Show with David Letterman," March 3,1998 on the CBS Television Network. Photo: Alan Singer/ CBS ©1998 CBS Broadcasting Inc. (credit:CBS)
Fresh Off 'The Fresh Prince' And Ready For 'Men In Black'(11 of17)
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Will Smith talks with Dave on "The Late Show with David Letterman," November 22, 1996 on the CBS Television Network. This interview was taped in Miami as part of the "Late Show Road Trip". Photo: Alan Singer/CBS ©1996 CBS Broadcasting Inc. (credit:CBS)
Steve Martin Hasn't Aged A Bit(12 of17)
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Steve Martin with David Letterman on the 5th Anniversary of "The Late Show with David Letterman," November 23, 1998 on the CBS Television Network. Photo: Alan Singer/CBS ©1998 CBS Broadcasting Inc. (credit:CBS)
Peter O'Toole Drinking And Smoking With A Camel (13 of17)
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Peter O'Toole makes a grand entrance riding a camel on "The Late Show with David Letterman," May 17, 1995 on the CBS Television Network. This show was taped in London, England. Photo: Alan Singer/CBS ©1995 CBS Broadcasting Inc. (credit:CBS)
Baking With Sophia(14 of17)
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Dave bakes a delicious tiramisu with Sophia Loren on "The Late Show with David Letterman," January 27, 1999 on the CBS Television Network. Photo: Alan Singer/CBS ©1999 CBS Broadcasting Inc. (credit:CBS)
Happy Birthday, Love Cher(15 of17)
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Cher feeds cake to Dave for his birthday on "The Late Show with David Letterman," April 12, 1999 on the CBS Television Network. Photo: Alan Singer/CBS ©1999 CBS Broadcasting Inc. (credit:CBS)
The One And Only Johnny Carson(16 of17)
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Johnny Carson in his first and only talk show appearance since stepping down as host of "The Tonight Show," gets a standing ovation by Letterman and the studio audience when he makes a surprise appearance on "The Late Show with David Letterman," in May, 13 1994 on the CBS Television Network. Photo: Tony Esparza/CBS ©1994 CBS Broadcasting Inc. (credit:CBS)
This Is What You Do When You Win The World Series(17 of17)
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The New York Yankees Shower Dave with champagne on "The Late Show with David Letterman," Oct. 28 1996 on the CBS Television Network. Photo: Alan Singer/CBS ©1996 CBS Broadcasting Inc. (credit:CBS)
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