People.com Entertainment TV Drew Barrymore Breaks Down in Tears as David Letterman Surprises Her During Her Birthday Show Drew Barrymore appeared on Late Night with David Letterman 20 times during its airing By Naledi Ushe Naledi Ushe Digital News Writer, PEOPLE People Editorial Guidelines Published on February 19, 2021 09:52 PM Share Tweet Pin Email Photo: The Drew Barrymore Show Drew Barrymore was overcome with emotion when David Letterman made a surprise appearance on her daytime show. Barrymore, 45, sat down with Savannah Guthrie in person and thought they were going to chat with Letterman, 73, via Zoom for her birthday episode airing on Monday. In a video released ahead of Monday's segment, the former Late Night host pretends to have technical difficulties before storming off and saying, "To heck with it. Forget this." "That's so sweet of him to do this. When was the last time you actually saw Dave?" Guthrie, 49, asks before Letterman appears on the set. Barrymore instantly covers her face and cries due to her shock to seeing Letterman. Drew Barrymore Says Her Kids Don't Like Her Films: 'They Call Them Mom Movies' "I'm so grateful that you're here," she says through tears. Letterman proudly shares that the "Zoomer thing" was his idea for the surprise. Barrymore appeared on the Late Night show 20 times throughout the shows airing from 1993 to 2015. Her most memorable appearance was in 1995 when she flashed the host for his 48th birthday. RELATED VIDEO: Drew Barrymore Explains Why She's Never Had Plastic Surgery: 'I'm a Highly Addictive Person' "From the moment I went on — especially with my little dance number, which was completely spontaneous and not calculated in any way — he let the audience know it was okay," Barrymore later told Entertainment Weekly in 2015 of that appearance. Never miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories. She continued, "He was so accepting of me, and letting everyone know to just go on the ride." "From that infamous show, we developed a really fun chemistry," Barrymore professed.