Former Head Writer of the Tonight Show Picks His Joke of the Week

Congrats to Jeff Sawyer for winning this week’s joke pick!

Pro comedy writer Joe Toplyn, Former head-writer of The Tonight Show with Jay Leno and Late Show with David Letterman, picks his joke of the week:

Winner: Jeff Sawyer, Follow him on Comedywire

Joe’s comments:

Setup: Blue Apron’s CEO is out

Punch Line: They’ll send him his stuff in a box next month.

Jeff used Punch Line Maker #1 — Link two associations of the topic — to create this great joke.

One handle of the topic, “Blue Apron,” a meal kit service, has an association like “get boxes in the mail regularly.”

The other handle of the topic, “out,” has an association like “fired,” which has a sub-association “pack up your personal belongings.”

Jeff’s punch line links those two associations by telling us that the CEO will get his stuff in the mail later.

Jeff had to decide whether the joke would be stronger if he ended on “next month” or on “in a box.” The latter option would have led to a punch line like, “Next month they’ll send him his stuff in a box.”

But that version wouldn’t have been quite as funny because the CEO getting his stuff in a box isn’t as surprising; plenty of fired executives have their belongings boxed up. The more surprising part is when the box is arriving.

Jeff also kept his joke short (Joke Maximizer #1) and clear (Joke Maximizer #4): his punch line consists of only ten words and each word has only one syllable.

Four-time Emmy winner Joe Toplyn is a former head writer for David Letterman and Jay Leno. He also wrote the book “Comedy Writing for Late-Night TV.”