World-renowned singing icon Sir Tom Jones is welcomed by Gavin to a night filled with playful banter and swapping stories of their legendary careers in the music industry.

Tom reveals to Gavin the extent of his humble start in Wales, detailing his early love for music through family gatherings and his school choir. He talks Gavin through his rise to success and recounts the pivotal moments from a career that has spanned nearly six decades. They then chew on some tender lessons learned from spending time with cultural icons like Elvis Presley and Frank Sinatra. The evening concludes with Tom and Gavin singing It's Not Unusual together acapella.

Gavin has invited over his friend Jack McBrayer — an actor and comedian beloved for his roles in film and TV such as 30 Rock, Wreck-It Ralph and Late Night with Conan O'Brien.

Jack reflects on his journey from small-town Georgia to Hollywood and recounts how Tina Fey gave him his big break when she wrote the iconic role of Kenneth Parcell on 30 Rock, especially for him. The two friends laugh while Gavin prepares their meals and commends Jack on his enduring positivity, something the comedian has become known for. Jack tells Gavin about the people that have most inspired him and the pair connect over ambitions for the future.