Tonight Show Woulda Shoulda Coulda: 15 Hours On Hold & Tinkerbell

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Jay Leno: Woulda Coulda Shoulda

Who has not second-guessed a comment, thought of a witty retort after the fact, or regretted a decision? We all have, and Jay Leno assembled a gang of experts to weigh in on these types of situations. This was The Tonight Show’s Woulda Coulda Shoulda segment.

The Tonight Show: Ross Mathews & Jordan Black

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Tonight Show Woulda Shoulda Coulda: 15 Hours On Hold & Tinkerbell

The Tonight Show’s Woulda Coulda Shoulda segment shared advice about recent weird news stories, such as the man who spent 15 hours on hold with Qantas Air.

Radio personality Jim Norton filled the role of Shoulda. Comedian Jordan Black was in the Coulda seat. Finally, Ross Mathews was in the Woulda chair for the night’s stories and scenarios.

In the first story, a Cambodian couple got divorced after 18 years. The judge told them to split their property equally, so the husband literally sawed their home in half.

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Tonight Show: Cambodia House Cut In Half

Ross Mathews said that he woulda looked on the bright side: “you can advertise it as half off.” Jordan Black said the man “coulda avoided a divorce if he was that good with all his tools.”

Finally, Jim said it might have been worse: you shoulda seen how they divided up the kid.”

Jay Leno: 15 Hours On Hold

An Australian man was on hold for 15 hours waiting for someone to answer the phone at Qantas airlines, only to find out that he was not even booked on the flight he was calling to confirm.

“There is no way I woulda stayed on hold for 15 hours for anything,” Ross Mathews said.

Jordan said he “coulda booked his flight on Virgin Airlines, ‘cause they never screw you.”

The Tonight Show: Tinkerbell Kicked Out of Disney World

A teen thought that she could make her trip to Disney World more special by dressing up as Tinkerbell and Peter Pan. After months of making homemade costumes, they were not allowed to enter the park. Then the disappointed girl cried on the news.

Ross Mathews said that once happened to him. Jordan Black said it is also hard for him to get into the park as a black man.

“I think she shoulda focused on the real problem: that her boyfriend looked more like Tinkerbell than she did,” Norton said.

Tonight Show: Stuck In Garbage Chute

A man got stuck in the garbage chute of an apartment building, falling three floors before getting stuck. Ross said given the size of the chute, he was impressed the guy fit in it at all.

Jordan thought this was a perfect example of “white trash.”

Jay Leno: Fishing Prison Sentence

A man is facing six months in prison for fishing in Austria. His defense was that he threw frozen fish in the water to impress his children.

Jordan said this could have all been prevented if the man had never had children in the first place.

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