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1* [[https://www.youtube.com/watch?v=R_0E7x3Nqys "I'd rather have a bottle in front of me than a frontal lobotomy"]], among many others.
2** In an interview he explains that when he went to a record store, he didn't get recognized at all. When he went to the dump, "Twelve guys surrounded my car."
3*** In another interview, when asked what his first instrument was, he replied, "I don't know... probably a box, or something."
4*** For that matter, go to Website/YouTube, search for "Tom Waits interview". Any one out of the whole bunch will contain a crowning moment of funny. The fireplace-shovel with the image of the devil on it, for instance. "It's like some kinda primitive e-mail."
5** "Step Right Up" , "The Piano Has Been Drinking" and "Pasties and a G-String" from ''Music/SmallChange''.
6*** "The Piano Has Been Drinking" has the line "the owner is a mental midget". The off-key piano playing just seals the deal on the song.
7** It borders on CloudCuckooLander behavior, but -- another CMOF came during the episode he guest-starred on John Lurie's [[http://en.wikipedia.org/wiki/Fishing_with_John fishing show]]. The two spend a couple days in Jamaica fishing for snapper, and the first time Tom catches one, he gives in to the impulse to put it down his pants. And leave it there for a while.
8* While on the surface level, it's [[DownerEnding heartbreaking]], if you have a dark sense of humor, Tom's rendition of [[https://www.youtube.com/watch?v=JYCDw89h0bo "Children's Story"]] in his scratchy, monotone voice and ending with, "Okay, [[WhatDoYouMeanItsForKids there's your story.]] [[CrossesTheLineTwice Night-night.]]" can be ''hilarious''.
9* It may be meant as a scathing satire, but many fans still say that "Frank's Wild Years" from ''Music/{{Swordfishtrombones}}'' is pretty damn funny.
10* The [[SpokenWordInMusic spoken word piece]] "Missing My Son" from ''Music/OrphansBrawlersBawlersAndBastards''. - though it's just his own variation on a well-traveled [[http://www.snopes.com/embarrass/dupe/checkout.asp urban legend]] that he's stretched into a ShaggyDogStory, there's just something about his delivery, as well as the fact that the deliberately underwhelming punchline is followed by a brief pause and a deranged-sounding wheeze of a laugh.
11* Watching a video that 'lip'synchs his song to footage of [[Series/SesameStreet Cookie Monster]].
12** Here's "[[https://www.youtube.com/watch?v=U5X4N2exOsU God's Away On Business]]", and here's "[[https://www.youtube.com/watch?v=fbiioBFkD_Q Hell Broke Luce]]"
13* The [[SerialEscalation increasingly ridiculous]] promises Tom makes for the unexplained product he's hawking in "Step Right Up."
14* The name of his song "That Feel" from ''Music/BoneMachine'', thanks to MemeticMutation.
15* Much of Waits' jokes and delivery during ''Music/NighthawksAtTheDiner''.
16* He has a song called "The Fall of Troy". Naturally, hardcore band The Fall of Troy named their first single "Tom Waits".
17* The "I was a chef" part from the "Hell Broke Luce" music video, with Waits wearing a chef's hat and a giant spoon on his left hand.
18-->[[Film/TwentyTwoJumpStreet And what was my name? It was Jeff]], [[PunctuatedForEmphasis JEFF!]]
19* "Diamonds On My Windshield" from ''Music/TheHeartOfSaturdayNight'' has the lyric which contains the expression: "colder than a well-digger's ass". Notable in that it's his first overtly humorous lyric in his overall discography.

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