Just months after retiring as host of the Late Show, the 68-year-old comedian reprised his beloved "Top 10" segment at the expense of presidential candidate Donald Trump. Surprising an audience in San Antonio, Texas that were in attendance at Martin Short and Steve Martin's A Very Stupid Conversation performance, Letterman presented a list of unknown facts about the former Celebrity Apprentice star.
"I am so happy to be out of the house!" a heavily bearded Letterman joked when he hit the stage. "I retired and I had no regrets, none. I was happy. I was complacent. I was satisfied. I was content. And then a couple of days ago, Donald Trump said he was running for president. I have made the biggest mistake of my life, ladies and gentlemen."
The longtime Late Show host held no punches when slamming Trump. "No. 10: That thing on his head was the gopher in Caddyshack," he quipped. "No. 9: During sex Donald Trump calls out his own name."
David Letterman comes out of retirement to slam Donald Trump with 'top 10' list
NEW YORK, UNITED STATES: US Vice President and Democratic presidential candidate Al Gore (R) with talk show host David Letterman 14 September, 2000 after the taping of Letterman's show at the Sullivan Theater in New York City. AFP PHOTO/ Luke FRAZZA (Photo credit should read LUKE FRAZZA/AFP/Getty Images)
NEW YORK, UNITED STATES: Republican presidental candidate and Texas Governor George W. Bush (L) poses for photographers with David Letterman after concluding taping of the 19 October 2000 Late Show with David Letterman in New York. Bush read the Top Ten list poking fun at what he might do if elected. AFP Photo by Paul J. RICHARDS (Photo credit should read PAUL J. RICHARDS/AFP/Getty Images)
BAGHDAD, IRAQ - DECEMBER 24: In this handout photo provided by the U.S. Air Force, 'Late Show' television host David Letterman entertains soldiers at the Coalition Provisional Authority headquarters December 24, 2003 in Baghdad, Iraq. (Photo by Reynaldo Ramon/U.S. Air Force via Getty Images)
NEW YORK - MAY 7: Tina Fey takes off her dress after her last appearance on the CBS Late Show with David Letterman, Thursday May 7, 2015 on the CBS Television Network (Photo by John Paul Filo/CBS via Getty Images)