In a throwback episode from 1997, David Letterman took on the challenge of guessing his mother’s Thanksgiving pies. This annual tradition had been going on for the past 15 to 16 years, showcasing Dave’s psychic ability to connect with his mom, Dorothy, and determine the type of pie she had baked for Thanksgiving.

As the show began, Dave expressed his admiration for his mom’s culinary skills, particularly her talent for baking pies. With a camera set up wherever his mom was celebrating Thanksgiving, Dave was determined to correctly guess the type of pie she had made, relying on their unspoken, unseen connection as mother and son.

As the Thanksgiving feast began, Dave took the opportunity to thank the staff and crew of “The Late Show” for their hard work and dedication on a holiday. With Biff Henderson and Tony Inky Mendes enjoying the spread of food, the atmosphere was filled with joy and excitement.

After weeks of not seeing his mom, Dave’s anticipation grew. The live broadcast connected him with his mom via CBS satellite, with Dorothy joining from St. Louis, Missouri. Dave greeted his mom and wished her a Happy Thanksgiving, engaging in light-hearted banter about being in the Gateway City.

Dave couldn’t help but ask his mom how their presence was received at their granddaughter Brin’s house, where they were celebrating Thanksgiving. However, Dorothy assured him that they were not ruining the festivities but instead having a wonderful time. She introduced her husband, Hans, and their granddaughter, Brien, along with her husband, Rob.

Curiosity got the best of Dave, and he inquired if the kitchen they were in was their actual kitchen. It turned out to be a borrowed one for the show. Dave then asked Dorothy to open the refrigerator so he could get a sneak peek at the pies she had prepared.

With the crew having a hearty appetite, some pies had already been devoured. But Dave was determined to guess the remaining pies. With a little help from swami music, Dave went into a slight trance to psychically divine the flavors of the pies.

For the first pie, Dave confidently guessed pumpkin, only to be corrected by his mom. Undeterred, he continued and suggested mince meat, but that wasn’t it either. Finally, Dave hit the mark with a coconut butterscotch pecan pie.

Moving on to the next pie, Dave made a few more attempts, guessing rhubarb and then sugar cream. But it turned out to be his favorite, cherry pie. The celebration commenced as Dave guessed correctly, giving credit to himself and savoring the taste of cherry pie.

As the segment wrapped up, Dorothy surprised Dave with a special presentation. She had made a stuffing head, showcasing her creativity and adding a touch of humor to the Thanksgiving celebration.

Through this entertaining and heartwarming segment, viewers got a glimpse of the special bond between Dave and his mom. Their connection transcended the distance between them, making for an unforgettable Thanksgiving celebration on “The Late Show with David Letterman” in 1997.

Although this episode is from years ago, it serves as a reminder of the love and fun shared during the holiday season. Dave’s mom, Dorothy, proved that her pies were not only delicious but also a source of joy and entertainment for all.