When you find yourself trying to remember a show (or any works) that's on the tip of your tongue but just out of reach, come here - the collective brain of the TVTropes community can probably help. Post all the details you can remember (examples help). If you're looking for a trope, head over to Trope Finder. Have general questions about tropes? Visit Ask The Tropers!
Unless someone else specifically remembers this episode and it's a different show, I think this is probably the one. IMDB doesn't have a lot about it but season 2 had an episode called "one for the kids".
Yes, definitely the second season of Last Comic Standing. I had to look up the cast to refresh my memory, but Jay London was the comic who bombed with the kids.
My dad used to put weird reality shows on TV to take a nap to. This would have been between 1999 and 2013.
It was an elimination based reality show. I am pretty sure that the big prize was to become a famous comedian or actor.
I only remember one challenge, where the contestants had to dress up as clowns and entertain a group of children while also presenting an educational message. They had to be both funny and engaging to the kids. I remember one male contestant had a really funny costume involving a tutu and pom poms, and all the kids laughed when he came out, but when he tried to give the educational message (don't play with matches or fire) it fell short. He shook his pom-pom halfheartedly while all the kids just stared with boredom.
What show was this??