Comedian Nate Jackson roasts The Uptown and earns a new fan in the process

December 10, 2024

Kelsey Webster,

Nate Jackson // Photo by Kelsey Webster

As a concert photographer, when we attended the Nate Jackson show at Uptown Theater on Friday, Dec. 6, we were expecting live music or at least a comedic musician. However, Nate Jackson and his four openers, Trenton Cotten, Nate Robinson, Soo Ra, and Kanisha Buss, delivered some of the best stand up that I’ve ever seen. Within the first four minutes of opening his show, Nate Jackson had earned a new fan.

He opened his show with a few minutes of standup before introducing his first opener, Trenton Cotten, and was making the crowd laugh so hard that we had tears running down our face before I’d even completely settled in our seat. Watching him interact with the crowd, and even directly call out a member of Uptown Theater’s staff while they were helping people get seated on the top level made it abundantly clear to me that he is going to knock it out of the park in his upcoming Netflix special.

He introduced each of his openers, Trenton Cotten, Nate Robinson, Soo Ra, and Kanisha Buss, and every comedian was somehow funnier than the last. Once it came time for his main set, our faces already hurt from laughing so hard and we couldn’t wait to see what he was going to do with the crowd work portion of his set. He laid out three ground rules to start off:

#1 – If you don’t want to be roasted, don’t make eye contact with him when he looks at you.

#2 – Don’t be a Karen and ruin the fun for everyone.

#3 – No matter who you have attended the show with, you are on your own if he starts to roast you.

The Proposal // Photo by Kelsey Webster

He roasted anyone and everyone mercilessly, yet good-naturedly, and he interacted with the audience with impressive ease. However, the most notable portion of the night was when Nate landed on one particular couple. A man introduced his significant other as, “my soon-to-be fiancée,” and when Nate questioned him further about the statement, the man said that he had the ring with him. Nate brought them both up on stage, he proposed, and she said yes!

The show ended with a segment that Nate has done repeatedly at his shows; He tries to matchmake with solo members of the audience by learning a little bit about them and pitching them to the crowd.

Overall, Nate’s crowd work, ability to pick up on details about each individual person that he roasts, and then transition into well-timed traditional standup is top tier, and we have been raving about the show to friends and family ever since.

All photos by Kelsey Webster:

Nate Jackson