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Straightforward trope -- the hero is that much cooler because he not only has a Cool Boat, he actually lives on it (in theory, the hero could live on an uncool houseboat, except that houseboats are almost inherently cool), making it, at the same time, a Cool House. This may be symbolic of the hero's cool detachment from things, since he could (in theory at least) just raise anchor and move his whole life away whenever he wishes. Doesn't apply to people who live on a boat which serves as the home base for dozens or hundreds of occupants, or to those who just work on a boat owned by someone else, even if that's where they spend their nights (in a navy, as a pirate, on a cruise ship).
- A pretty popular Archie story involves one. Archie and Betty find a girl in a swamp, and take her to their friend, an old captain living in a houseboat. The girl is revealed to be an heiress, but her uncle is trying to kill her. Archie and his friends set a trap for him, luring him to the boat, planning on jumping him when he opens the door. However, the uncle decides instead to cut the lines, sending them down toward the Inevitable Waterfall. Of course, the gang had planned for this, and there was a cable that kept the boat from drifting too far down. Makes you wonder why the captain lived so close to a waterfall...
- Blood Work (Clint Eastwood lives on one); but so does the Big Bad, berthed a few slips down.
- Parodied in The Simpsons Movie: Captain McAllister, to escape from Lisa's environmental door-to-door campaigning, sent his houseboat down the river.
- In You've Got Mail, Tom Hanks' character and his father and grandfather all have boats. However, they only use them to sleep in when they get kicked out of their apartment by a girlfriend.
- The Commodore in the 1980 Popeye lived on a boat.
- Well, it is about sailors.
- In Father Goose, The Protagonist starts out as this, but is stranded on an island and spends a fair amount of the movie trying to fix his former home.
- The undercover cop in Hard Boiled lives on a yacht (which ends up the site of one of the film's gunfight set pieces).
- Lorenzo Lamas's character in Snake Eater drives a houseboat.
- Cocktail: Bryan Brown lives on a yacht.
- John Wayne in Mc Q.
- Riggs, in at least one of the Lethal Weapon movies.
- Travis Mc Gee, from the novels by John D Mac Donald, lives on a houseboat called "The Busted Flush" (he won it in a poker game).
- John Kelly in Tom Clancy's Without Remorse has a very nice houseboat, IIRC, until he destroys it at the end as part of faking his own death.
- In Jim Butcher's Dresden Files novel Changes, Harry is living on a houseboat at the end. Briefly.
- In Jasper Fforde's Lost In A Good Book, Thursday Next moves into one at the end of the book.
Live Action TV
- The early '60s detective series Surfside 6 had its heroes living on the title boat in Miami Beach (cha-cha-cha, CHA).
- Quincy lived on a boat, until the episode "Quincy's Wedding, Part 2" when he arranged to sell it, because his fiancee and soon-to-be-wife Emily didn't want to live on it.
- Miami Vice (Crockett had two boats, one for racing, one where he lived with his alligator).
- On Simon and Simon Rick lives on a boat parked in A.J.'s front yard.
- MacGyver lived on a houseboat for several seasons.
- Duncan MacLeod in Highlander the Series lived off and on in one of these in Paris.
- Bobby from Cougar Town lives on a boat. A boat that never leaves the parking lot.
- In the second season, Jules and the others move it to the marina to surprise Bobby. It promptly sinks. They do fish it back out, leaving Bobby back where he started.
- At the end of the season, Bobby moves into an apartment and leaves the houseboat to a depressed Travis. In the third season, Travis moved to a dorm and Bobby is back on the boat.
- Cody in Riptide runs the series detective agency out of his boat; his partners Nick and Murray live on the boat as well.
- On the Animal Planet show Pit Boss, main character Shorty lives on a boat. With pit bulls. It's a reality/documentary thing about a group that rescues abandoned pit bulls, so he fits the "heroic" requirement too.
- Kellerman from Homicide: Life On the Street. Of course his coolness got deconstructed as time went on.
- GOB Bluth made a hearty attempt at this trope, but the boat belonged to the Bluth Company, and his residency there was one of the strings that kept him (in his mind) beholden to his brother Michael.
- Sam and Fiona were nearly caught snooping around on the boat belonging to the week's villains. This one's a two-fer, actually, since...
- ... the villains were a couple running various financial scams while living out of the boat precisely so they could take off on a moment's notice, and...
- ... when they were about to be caught by the villains, Sam pretended to be a guy claiming he lived on the boat in order to score with Fiona.
- A rare female example: Kate from Fairly Legal. Although she admits in the first season finale that she doesn't actually sail.
- Endless Ocean's base of operations for your character is the trusty Gabbiano.
- Derelict: The main character's base of operations.
- In the first season of Avatar: The Last Airbender, Zuko lives on a small, crappy warship. Also more of an example of Houseboat Villain than Houseboat Hero.