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

Congrats to Scott Benjamin 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: Scott Benjamin, Follow him on Comedywire

Joe’s comments:

Setup: A booby-trapped wheelchair shot an FBI agent at a house rigged to ambush intruders

Punch line: Home Alone XXVII: Kevin’s Final Showdown

Scott’s great joke is an example of Punch Line Maker #2: Link the topic to pop culture.

Usually when you’re trying to use Punch Line Maker #2, you start by identifying a handle of the topic, like “wheelchair.” Then you brainstorm associations of that handle and see if any of them suggests something in pop culture.

For example, “wheelchair” might suggest the late physicist Stephen Hawking, so maybe there could be a punch line about Stephen Hawking and the Big Bang theory.

But this topic is so full of attention-getting elements that it’s hard to pick one or two that you’re pretty sure the audience will focus on. So instead, Scott treated the entire topic as a handle and asked himself what in pop culture that crazy scenario suggests. To him, it suggested some version of the movie “Home Alone.”

Then Scott factored in the handle “shot an FBI agent,” which has the association “desperate criminal.” Combining that association with “Home Alone” led him to his punch line naming the last in a long line of increasingly over-the-top sequels.

Notice that Scott didn’t just go with a generic punch line like, “Sounds like a sequel to ‘Home Alone.’” He used Joke Maximizer #9 — Get specific — and gave us a movie title packed with details.

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.”