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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
- 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).
- Retcon: Minor Example. In the original LSL 1, Larry is stated to be 38 years old. The VGA version changed this to 40 only for Reloaded to change it back to the original age. To add more confusion, the hintbook for LSL 3 states Larry is 43 while all future games refer to Larry as 40.
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.
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.
In the Land of the Lounge Lizards
LeftyThe diligent bartender and owner of Lefty's Bar.
The PimpA pimp working in the back room of Lefty's Bar.
The ProstituteAn unnamed woman working on the second floor of Lefty's Bar and perhaps the only optional sexual encounter in any Larry game.
- Fan Disservice: She tends to be drawn as unattractively as possible while still being just attractive enough to retain her current line of work.
- Kaizo Trap / Hope Spot: Since the end goal of the game is to lose your virginity, players may feel like they've won the game once they have sex with the prostitute. However, doing so without a condom leads to a Non-Standard Game Over, and even with the condom, Larry doesn't feel like doing the deed with a prostitute counts.
- Smoking Hot Sex: After Larry does the deed with her, she pulls the covers up and begins smoking a cigarette. Of course, the flavor text implies that she enjoys the cigarette more than she enjoyed Larry.
FawnA girl located in the disco club. Highly materialistic and low on morals.
Shape Up or Slip Out
GaryThe towel attendant located in the resort's spa lobby.
- Camp Gay: A very intentional example.
- Non-Standard Game Over: If you offer your room key to Gary, he'll take it as an offer to sleep with him, but you'll get it back. Do it a second time, and the game ends with Larry and Gary walking off into the sunset together.
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 DykeHangs 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 EleetaWorks 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.
ShableeHangs 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 PayneShamara 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 in the following game.
- 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.
Love for Sail
Victorian PrinciplesThe 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 JuggA 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 BaringmoreAuthor 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 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.
PeggyThe ship's foul-mouthed peg-legged pirate-ish handywoman.
- As Himself: Is listed as such in the credits. She's actually voiced by Mary Kay Bergman, but requested not to be credited due to her foul language.
- Every Device Is a Swiss-Army Knife: Her stump can have various things attached to it, from mops to fishing poles.
- Sir Swears-a-Lot: She claims to have "Cloret's".