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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: His only priority is sex. Even when he's given the majority share of an oil company for accidentally killing its owner by his gold digging wife, he's disappointed that she doesn't sleep with him.
- 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.
- Butt-Monkey: Even ignoring his many, many, MANY, possible deaths, Larry is repeatedly put through dangerous situations (like being chased by the KGB) and humiliated (see having to not only dance on stage in a showgirl's outfit, but also wear that outfit in front of an attractive attorney to trigger an Optional Sexual Encounter).
- Casanova Wannabe: The series might as well be called Casanova Wannabe: The Game. In fact, Larry himself is the former Trope Namer.
- Kavorka Man: That said, Larry actually repeatedly has sex with (or gets started on it before his classic bad luck kicks in) gorgeous women throughout the games.
- Catchphrase: "I wish I had a dollar for every time I heard that!" after some sexually ambiguous remark.
- Disco Dan: Who else?
- Gonk: All versions of Larry are short, balding and cartoonish looking compared to the other characters in the games.
- 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).
- Nice Guy: He's fairly easy-going and polite, even to people he's not interested in pursuing. Well, most of the time.
- 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.
- Teeny Weenie: Should you flash yourself to other people in Reloaded, many will comment on Larry's less than impressive package.
- You Need a Breath Mint: Despite putting on breath spray, it fails to cover up the horrible odor of his breath, as many of the girls and general public alike will point out in Reloaded.
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. Also appeared in spinoffs.
- 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.
- Butt-Monkey: Like her male counterpart, she's goes through both lethal and non-lethal abuse.
- Child Hater: Suggested from the narration's comment on a stage hazard in LSL 3's log ride sequence that appears to be a baby using a flotation device:Narrator: "Lookout, Patti! It's your worst nightmare! Children!"
- Chuck Cunningham Syndrome: She appeared in the third and fifth games, along with spinoff material released at the time like Larry's Big Score. After that, she was never seen again (not physically anyway, accounting for her cameo in LSL 6 as a calender pinup model). The Official Book of Leisure Suit Larry suggests she and Larry were still seeing each-other during the events of LSL 6, but LSL 8 has Larry pine for her in Lefty's Too (possibly hinting at the two having a falling-out or some other situation making them end their relationship).
- Distaff Counterpart: In many ways she can be called a female version of Larry. From her color scheme (not only her white dress in LSL 3 but also sharing Larry's skin and hair colors), promiscuity, Butt Monkey moments, even having to complete sections of games by using random objects.
- Early-Bird Cameo: Officially makes her debut in LSL 2 as Dr. Nonookee's pianist, under the name Polyester Patti.
- Going Commando/Vapor Wear: LSL 3 has points that require Patti stripping off her clothing (or pieces of it) to complete them. The first to be removed being her panties. After a point in LSL 3's ending where she and Larry are floating in Sierra's Space Quest section, the two of them fall on their faces once the anti-gravity generator is disabled which ends up exposing Patti's underwear less bottom (complete with her crotch getting shadowed out).
- 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. Even when listing just non-lethal situations she's been put through abuse like falling off a bungie cord made from panty hose until landing face-down.
- Woman in White: Certainly in the third game, where she wears a white dress. Also fits her role as Larry's female counterpart considering how he wears a white leisure suit.
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.
- Deadpan Snarker: He doesn't miss a chance to sarcastically rip on Larry.
- Interactive Narrator: Him and Larry sometimes get in arguments with each other. In LSL 7, Captain Thygh can even hear him at one point.
- Lemony Narrator: He has an exceptionally low opinion of both Larry and the Player and makes no secret of it.
- What the Hell, Hero? / What the Hell, Player?: He drops several of these throughout the series.
In the Land of the Lounge Lizards
LeftyThe diligent bartender and the owner of Lefty's Bar.
The PimpA pimp working in the back room of Lefty's Bar.
- All Men Are Perverts: To get past the him, you have to change the channel on the TV he's watching to a porno station.
- American Accents: Seems to speak with a heavy Brooklyn accent, despite the game being set in a parody of Las Vegas.
- Joe Sent Me: The password to get in is "Ken Sent Me", a reference to Sierra developer Ken Williams, who worked on the game.
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!
Gary FairyThe towel attendant located in the resort's spa lobby.
- Camp Gay: A very intentional example.
- Gay Option: Although it results in a game over.
- 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. The same thing can happen (much quicker, too) by flat out unzipping your pants in front of 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: 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. She doesn't seem to operate on safeword rules.
- 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 resort's 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!
- 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 transvestite (and a man, not a 'transgender'/'transwoman') by the gigantic erection he gets as he and Larry are about to have sex (and the game's jokes are very specific that he is a 'man', and that is why he knows what a 'Man" likes). Larry doesn't respond well to it, but he is completely unfazed by his reaction, as he now makes Larry his bitch (rape). The official hint book even throws in a gay joke implying that Larry might have enjoyed it more than he let on. The design documents are very specific that he is a transvestite, and actually a man. It goes as far to call him a 'he/she' and a 'girlie-man', and Larry's "first admitted homosexual experience".
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, but give her something steamy to read and she really lets loose.
- 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.
- The Glasses Gotta Go: She ditches her glasses because they kept steaming up on her during sex.
- 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.
- Sex God: After her change, she brags to be the most sexually knowledgeable person on the ship. Larry can use her to win the sex meter challenge sending her into the booth in his place and she attains a score so high that it breaks the machine.
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.
- Buxom Is Better: The Juggs have some of the largest breasts in the entire franchise. Needless to say, when Larry attempts to ask about them, the two immediately think he's about to compliment their giant hairdos.
- Meaningful Name: The Juggs have...take a guess.
- 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.
- My Eyes Are Up Here: Some dialogue options are shown from Larry's point of view as his vision pans down slowly. She'll call him out on it before he can get to her nipples unless the player has found the earplugs.
- 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.
- Shameless Fanservice Girl: She spends her entire cruise naked by the pool, even getting the purser to lock her clothes away so she can't leave. Even the one occasion she's dressed in the game, she wears hot pants and a small top.
Captain ThyghThe captain of the HMS Bouncy. Whoever wins her contest spends the rest of the cruise in her cabin.
- Ambiguously Bi: There's at least one female competing in the contest.
- 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", if Peggy is to be believed. 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. Then there's the fact when Larry meets the winner of last week's contest, he's being wheeled out of Thygh's cabin in a gurney.
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".