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Voiced by: Jan Rabson, Jeffrey Tambor (Box Office Bust)The series lovable protagonist.
- Alliterative Name: Larry Laffer.
- All Men Are Perverts
- A Man Is Not a Virgin: Before his 38th birthday, Larry actually had no interest in women or sex, but then his brain went into a sexual panic mode due to the lack of action, thereby setting the goal of the first game. And just to make sure you actually do the deed, if Larry is still a virgin by sunrise (which takes a few hours of game-time), Larry will commit suicide.
- Basement-Dweller: Or used to be. The only reason he finally moved out of his mother's house, was because she sold it before going on a long vacation.
- Bond, James Bond: Larry usually introduces himself as "Larry; Larry Laffer". When the games get voiced, he does a short chuckle for the semicolon.
- Casanova Wannabe: The series might as well be called Casanova Wannabe: The Game. In fact, Larry himself is the former Trope Namer.
- Catchphrase: "I wish I had a dollar for every time I heard that!" after some sexually ambiguous remark.
- Disco Dan: Who else?
- Loser Protagonist
- Lovable Sex Maniac: You don't say...
- Really a lot more "lovable" than "maniac". Given the series' reputation, you'd be surprised by 1) how little actual sex is in the games, and 2) how ready Larry is to drop the swinger lifestyle for the idea of true love (usually once per game).
Passionate PattiA love interest for Larry in games 3 and 5. She also served as a second playable character in these games after the man himself.
- Black Face: An unintentional example happens when she gets on the bad end of a malfunctioning copy machine. Though it makes for a good disguise.
- Chuck Cunningham Syndrome: She appeared in the third and fifth games. After that, she was never seen again.
- Early-Bird Cameo: Officially makes her debut in LSL 2 as Dr. Nonookee's pianist, under the name Polyester Patti.
- Improvised Weapon: She rather impressively manages to KO a feral pig with her bra and a pair of coconuts.
- Ms. Fanservice: Of course.
- Single Woman Seeks Good Man: Quite possibly the nicest love interest that Larry has ever had and the only one to stick with him through to the end of both games.
- Slapstick Knows No Gender: She's just as vulnerable to being comically killed as Larry.
- Woman in White: Certainly in the third game, where she wears a white dress.
FawnFrom In the Land of the Lounge Lizards. She is located in the disco club. Highly materialistic and low on morals.
- Gold Digger: Oh yes! Her "modest" demands includes a lot of cash for a cheap-ass wedding and a diamond ring.
- Ungrateful Bastard: She dumps Larry for having to pay (so to speak) for a bottle of wine after receiving a lot of gifts from him.
Merrily LoweFrom Shape Up or Slip Out. A redhead who is addicted to bungee jumping.
- Fiery Redhead: Subverted. She's not especially aggressive, but she is exceptionally passionate and does play up her bungee addiction to be more serious than drug addiction.
- Koan: Knows one that is apparently shocking enough to cause Larry to fall off the bungee tower.
- Name's the Same: Likely not related to Al Lowe in any way.
- Punny Name: Named for Merlot.
- Redhead In Green: She's obviously a redhead and wears a thin green bikini.
Christina Priscilla Diana "Thunderbird" Van DykeFrom Shape Up or Slip Out. Hangs around La Costa Lotta's gym. A notorious dominatrix.
- Bondage Is Bad: Well it certainly is when she's at the helm.
- Hell-Bent for Leather: Her outfits seem to mostly revolve around leather.
- Overly Long Name: It causes Larry to wonder if he has to remember all of it. Thankfully, the answer to that is "no".
- Punny Name: Named for Thunderbird wine. Plus, with her real name, Van Dyke, she is quite butch.
Rose EleetaFrom Shape Up or Slip Out. Works La Costa Lotta's high colonic treatment suite. Has some difficulties with English.
- Ass Shove: Given that she works in the high colonic treatment suite, this is inevitable.
- Funny Foreigner: Her English-speaking skills leave something to be desired.
- Latin Lover
- Punny Name: Named for Rose wine.
ShableeFrom Shape Up or Slip Out in the La Costa Lotta's Make Up Class. Loves shopping and wants a dress.
- Black Is Bigger in Bed: It nearly reaches up to her bustline!
- Dropped a Bridget on Him: She's actually trans. Larry doesn't find out until right before they have sex.
- Pretentious Latin Motto: Veni, Vidi, Visa: I came, I saw, I shopped.
- Punny Name: Named for Chablis wine.
- Unsettling Gender Reveal: "She's" revealed to be transgender by the gigantic erection she gets as she and Larry are about to have sex. Larry doesn't respond well to it, but she's completely unfazed by his reaction.
Shamara PayneThe "Final Girl" in Shape Up or Slip Out. Shamara has come to La Costa Lotta to do some soul searching.
- Defector from Decadence: She has everything she wants in life, but came to La Costa Lotta to find out if she was truly happy. She relapses immediately at the start of Love For Sail and decides money is what makes her happy.
- Face–Heel Turn: Having sex with Larry for one night causes her to become bitter and run off with his money.
- Shameless Fanservice Girl: She is almost absolutely naked save for sheer leggings and a slightly less sheer thong. Justified in that it fits her motif of a girl who shed off all her material belongings to search for the source of her happiness.
- Punny Name: Named for Champagne.
- Took a Level in Jerkass: Apparently one night with Larry was enough to do it.
Victorian PrinciplesFrom Love For Sail. The ship's librarian. Very prudish and uptight.
- All Women Are Prudes: Well, THIS one is, anyway. The book she's reading is even called "Prudish and Proud"!
- Bookworm: Supposedly she's on her third run through most of the ship's books when you speak to her. The stack of books next to her is something she'll supposedly finish in bed that night.
- Hot Librarian: Well, not at first... It's amazing what a change in reading material will do to you.
- Punny Name: She's a parody of actress Victoria Principal.
- Really Gets Around: After you switch books on her, her dialogue and character change to reflect this.
Wydoncha and Nailmi JuggFrom Love For Sail. A mother and daughter country duo. The Juggs are on the HMS Bouncy to lay low after an "incident" at one of their concerts.
- Absurdly Youthful Mother: Nailmi. So much so that she had to tell Larry who was who. She apparently had Wydoncha on her first ovulation.
- Punny Name: They're named after (and a parody of) Wynonna and Naomi Judd. Also, their names combined are a homonym of "Why don'cha nail me?"
- Too Much Information: Wydoncha tends to spill some rather...personal information regarding the two.
- Verbal Tic: Nailmi has one of these, don'cha know?
Drew BaringmoreFrom Love For Sail. Author of the book Fokker: More Than Just an Airplane. Spends most of her time lounging by the ship's pool dressed in nothing but her laptop.
- Bookworm: Not so much as Victorian, but then again, she IS an author.
- Naked People Trapped Outside: Did so willingly. She had the crew lock her luggage containing all her clothes down in the forward hold so she could lounge by the pool all day.
- Punny Name: She's a parody of actress Drew Barrymore.
Captain ThyghThe main conquest in Love For Sail, and the captain of the HMS Bouncy. Whoever wins her contest spends the rest of the cruise in her cabin.
- Punny Name: Her name is a pun of William Bligh, famous for his involvement of being mutinied while commanding the HMS Bounty.
- Really Gets Around: Her nickname is "Captain Cocksucker". The hallway into the employee's lounge is decorated with pictures of her previous conquests to the point that there's almost no bare wall visible. Not to mention the winner of last week's contest has to be wheeled out on a stretcher.
Voiced by: Neil Ross (Shape Up or Slip Out, Love for Sail!), Brad Venable (Reloaded)The Narrator for all the games, but given voice for Shape Up or Slip Out, Love For Sail, and Reloaded.
- Interactive Narrator: Him and Larry sometimes gets in arguments with each other.
- Lemony Narrator: He has an exceptionally low opinion of both Larry and the Player and makes no secret of it.
PeggyFrom Love For Sail. The ship's foul-mouthed peg-legged pirate-ish handywoman.
- As Himself: Is listed as such in the credits. Most believe her actual actress is Susan Silo, due to sounding similar to her role as Helen Back from Freddy Pharkas: Frontier Pharmacist.
- Every Device Is a Swiss-Army Knife: After losing her leg, her stump can have various things attached to it, from mops to fishing poles.
- Sir Swears-a-Lot: She claims to have "Cloret's".