Girl of the Week: True, but none of them ever converted their boat into a treehouse!
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 always inherently cool), making it, at the same time, a Cool House. This may be symbolic of the hero's cool detachment from things (or his being Allergic to Routine), 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).
In Real Life, houseboats are typically mobile homes on pontoons or barges, and are as close to Cool Boat as The Alleged Car is to Cool Car. Some works with Loser Protagonists will have the hero live on such a houseboat to highlight their lack of social skills.
- 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...
- Tempest Gale in Pk2 lives on a small, crappy boat.
- Blood Work (Clint Eastwood lives on one); but so does the Big Bad, berthed a few slips down.
- 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 McQ.
- Shane Falco in The Replacements (2000) ("See that yacht over there with the satellite dish? Mine's the one next to it covered in pigeon crap.")
- Leon Phelps, the title character of The Ladies Man lives in a beat up old houseboat full of painfully Seventies decor.
- In Assault on a Queen, Mark Brittain and Linc Langley live on their fishing charter boat. When the owner the marina threatens to impound their boat for nonpayment of fees, Mark agrees to sign on to Rosa's expedition as diver.
- Travis McGee: The title character from the novels by John D. MacDonald lives on a houseboat called The Busted Flush (he won it in a poker game), parked in Slip F-18, Bahia Mar Marina, Fort Lauderdale, Florida. The marina is real (although there hasn't been a Slip F-18 since their last renovation), and maintains a plaque dedicated to the hero and his chronicler.
- John Kelly in Tom Clancy's Without Remorse has a very nice boat he uses to live on when he's not on the island he rents, until he destroys it at the end as part of faking his own death.
- In Jim Butcher's The Dresden Files novel Changes, Harry is living on a houseboat at the end after his apartment is burned out. Briefly. Then after he's revived he moves into a shack on a hidden island.
- Jasper Fforde:
- The protagonist CDR Mike Montgomery in the novel Scorpion In The Sea. When he isnt on the US Navy destroyer he is the captain of. The author of that book prefers this trope. The protagonist Jim Hall in another novel Darkside also lives on a houseboat.
- The early '60s detective series Surfside 6 had its heroes living on the title boat in Miami Beach (cha-cha-cha, CHA).
- Quincy, M.E. 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 has two boats, one for racing, one where he lives with his alligator.
- On Simon & Simon, Rick lives on a boat parked in A.J.'s front yard.
- MacGyver (1985) lived on a houseboat for several seasons.
- Duncan MacLeod in Highlander: The Series lived off and on in a péniche on the Seine in Paris.
- Bobby from Cougartown 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 moves 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.
- Arrested Development: 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.
- Burn Notice: 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 ...and in the season two premiere her boat blows up.
- Joe and Brian accidentally sink Lowell's houseboat on Wings.
- Harrow lives on his sailboat anchored on the Brisbane river.
- Endless Ocean's base of operations for your character is the trusty Gabbiano.
- Assassin's Creed plays with this trope in games that feature/revolve around sailing:
- In Assassin's Creed IV: Black Flag, Edward makes the Aquila his base of operation at least until he takes the island of Great Inagua under his control from an Templar agent.
- Assassin's Creed: Rogue averts this: while Shay uses the Morrigan much like Edward, he also gains a mansion residence in New York immediately after joining the Templars.
- Played straight in Assassin's Creed: Odyssey where the Misthios make their ship the Adrestia as their residence after leaving their childhood home in Kephallonia.
- Suikoden V has the Oboro Detective Agency, whose members live together on a small boat as both coworkers and surrogate family. This lets them pick up and go whenever they want; if the player isn't careful, this can lead to them being lost forever, courtesy of them leaving before the Prince can convince them to join his cause.
- Derelict: The main character's base of operations.
- Donald Duck:
- "Hero" is questionable, but in The Little Wise Hen, the very first Donald Duck shorts, he lived on a houseboat. Fittingly, since he was more of an actual duck back then, so you'd think he'd live close to water.
- His house at the Disney Theme Parks is a boat, called the Miss Daisy, which was carried over into the Mickey Mouse Works shorts.
- In DuckTales (2017), Donald and his nephews are living in an old boat. By the end of the pilot, it relocates to Scrooge McDuck's swimming pool after it catches fire due to the nephews trying to hotwire it.
- The Simpsons:
Homer: Oh, come on, Marge. You've always wanted a house by the lake. And besides, if you don't like your neighbors, you just lift anchor and sail away!
- Once, the family moves to Terror Lake as part of a Witness Protection deal in which they become The Thompsons.
The Simpsons: [laughing]
[all the other houseboats sail off as quickly as possible]
- Chief Wiggum lives on one (The Big Queasy) in the Chief Wiggum, P.I. segment from The Simpsons Spin-Off Showcase.
- In the legal case of Lozman v. City of Riviera Beach, Lozman was a local political troublemaker who lived in a houseboat, which was condemned and destroyed by the city in an effort to get rid of him. He filed a lawsuit and had to take it all the way up to the Supreme Court before he won his case, using his winnings to buy a new houseboat which he sailed right back into the town.