Sassy Secretary

Cracking gum and cracking wise. Often with a very nasal voice, usually with a Joisey or Brooklyn accent.

Dates back to the 1930s at least, with Sam Spade's secretary and Joan Blondell in any number of movies, making this Older Than Television.

May also be a Sexy Secretary or a Plucky Office Girl. Due to the interpersonal nature of the role, they may be The Face of their group.

Examples of Sassy Secretary include:

Comic Books

Any and all depictions of Tony Stark's secretary Pepper Potts.

Film

Moneypenny from the James Bond movies. She only fits the "cracking wise" personality though.
Janine Melnitz in every incarnation of the original Ghostbusters series, including both movies.
- On the other hand Kevin, her counterpart from the 2016 reboot, doesn't have enough brainpower to understand what sass is, let alone deliver any.
Grosse Pointe Blank might be considered a subversion, as while John Cusack's character has such a secretary (played by his sister, Joan), he is an amoral assassin.
- Moreover she herself is an effective operative, rattling off info from dossiers, dressing down people over the phone, and nonchalantly dousing the office in gasoline when it's time to move on.
Pamela Finklestein from UHF.
Skinner's secretary in Hot Fuzz.
Not a secretary, but Birdie from All About Eve acts as Margo's valet - and boy, is she a wisecracker...
Rockwell's mayor's secretary in The Iron Giant.

Literature

Classic literary example: Velda from Mickey Spillane's Mike Hammer novels.
Cathy, John Taylor's secretary in the Nightside series of books.
Connie in the Stephanie Plum series of novels. She has Mob connections, an impressive collection of weapons in her desk (on at least one occasion, she threatens to use one on lecherous boss Vinnie), and a "take no crap" attitude that serves her very well dealing with her colleagues.
Effie Perine from the Sam Spade novels by Dashiell Hammett. Probably the Trope Maker.
Sir John's clerk Mrs Pound from Darkness Visible is sassy enough to deliberately wind up Lewis when she has information he needs to prevent the end of the world. Of course she's going to give it to him, but not until he realises how damned hard it was to get...

Live-Action TV

Vicki Lewis ("Beth") on News Radio reportedly feuded with Kathy Griffin because of her similar redheaded character on Suddenly Susan. It is worth noting that Griffin's character, while a complete ripoff of Lewis's from the standpoint of personality, is not actually a secretary.
- And Vicki Lewis is actually talented and funny.

Beth: Mention that there's a spunky redhead in this office.
Joe: I don't know how to tell you this, but there's a spunky redhead in every office.
Beth: Tell me about it.

- She shouldn't have been so upset about one character being like her character, so much as for most of The Nineties approximately 80% of the shows on NBC were about single people working at a media outlet in a big city. They all had a character that was exactly like hers.
Flo the waitress from Alice, another non-secretary example.
Karen on Will and Grace.
- And Mr. Doucette's secretary, Mrs. Freeman. Also a Sassy Black Woman.
Carol from The Bob Newhart Show.
Jennifer from WKRP in Cincinnati.
- Ahem... she is a receptionist, not a secretary thankyouverymuch.
Sam (played by Mary Tyler Moore's legs and voice) in Richard Diamond, Private Detective.
Frannie Vecchio on Due South.
Christina Hendricks' character Joan on Mad Men.
- Ditto (more or less) for the Sterling Cooper phone switchboard operators, Lois, Marge, Ivy, and Nannette. Kinda makes sense, particularly given that Marge and Nannette are both played by comedians: Marge by Stephanie Courtney, a member of The Groundlings best known as Flo of the Progressive Insurance commercials and Nannette by Kristen Schaal, who is, well, Kristen Schaal.
Patti from Eli Stone.
Amanda the receptionist from Ugly Betty.
Saeko Mizuki from Glass Mask.
Greg's secretary on Dharma and Greg. (Played by Yeardley Smith, natch.)
On The West Wing, Leo McGarry's secretary, Margaret, and Josh's assistant, Donna Moss, have elements of this.
- Mrs Landingham is a Cool Old Lady version.
Whenever Picard adopts the persona of Dixon Hill in the holodeck on Star Trek: The Next Generation, he gets his own Sassy Secretary.
A rare male example: Dennis Finch (David Spade) on Just Shoot Me (though he denies being a secretary, at least at first).

Finch: (answering phone) Blush magazine, underpaid phone monkey speaking.

- Oddly enough, Russell Dunbar (also Spade) has his own rare male example, Timmy, on Rules of Engagement.
John Inman in Take A Letter Mr Jones
Toby in Dream On. Need we go on?

Newspaper Comics

Carol, the Pointy-Haired Boss's secretary from Dilbert
- Except that she takes "sass" Up to Eleven straight into pure misanthropy and narcissism.
- And for a while she has a crossbow.
Ms. Blips, the competent counterpart to Sexy Secretary Ms. Buxley in Beetle Bailey, has always filled this role, although in more modern strips, Buxley often does as well.

Tabletop Games

Lolth has one. No, seriously, the dreaded Demon Queen of Spiders of Dungeons & Dragons has a Sassy Secretary, and Player Characters have to deal with her in the epic adventure Vault of the Drow (from way back in 1980). Seriously. When the players reach the room with the sole access to Lolth's throne room, they find a Type V demon (called a marilith in later editions, a very powerful six-armed female fiend with a snaky lower body) at a messy desk who insists they sign in before they confront Lolth, and then wait while she finds the ledger. (Craziest part? If the PCs comply, she lets them in with no argument! If they don't wait, they'll have a much harder time getting in, not just from fighting her, but triggering an alarm and increasing the probability of random encounters. Doing what the secretary says lets them conserve their power for Lolth herself, who is no pushover.) No explanation is given for this and if the players ask, the demon just says "Lolth told me to". Maybe this demon is just being punished for some slight by being given a job that chaotic fiends would likely hate, but that's just conjecture.
- The demon secretary appears in a Nodwick strip much later that parodies the adventure, resembling a more traditional secretary, a snarky coffee addict using a laptop. She's sassier and ruder than the one in the source, and not all-too-good at her job, more occupied with playing solitaire on the computer than dealing with the heroes, who eventually sneak past by leaving dummies in the waiting room.

Theatre

Miss Marmelstein (who hates being on a last name basis with everybody) from the musical I Can Get It For You Wholesale. (The role was created by Barbra Streisand in her first appearance on Broadway.)
Molly Grant from One Touch of Venus.

Video Games

Eva from Grim Fandango.

Manny Calavera: It's my boss's secretary, Eva.
Eva: It's my boss's whipping boy, Manny.

Manuel Calavera:: Any messages for me?
Eva:: No, calls stopped coming for you the day you left. They're STILL sending you that lingerie catalog, though.

Manuel Calavera:: Busy as ever, I see.
Eva:: I'd have more work to do if you had more clients.

World of Warcraft; play as a Goblin, and your character starts out as something of an executive with a secretary whose very name - Sassy Hardwrench - emphasizes the Trope. Despite her snarkiness, however, she is the only employee who does not double-cross the Player, and the Only Sane Goblin in Kezan. Even if, like most of them, she has a thing for explosives.

Web Comics

In Schlock Mercenary Ventura had a warship AI personality and avatar crafted in such an image on purpose -- expecting that this will make the Captain think before he opens mouth more often.

Western Animation

Transformers Animated features a robot that has apparently been programmed to act like one of these.
Laura from Dr. Katz, Professional Therapist qualifies, but she's extremely rude and useless as a secretary. She doesn't take messages, and refuses to bring Dr. Katz coffee.
In the My Little Pony: Friendship Is Magic episode "Hearths Warming Eve", Chancellor Pudding Head's secretary Smart Cookie is portrayed as quite the snarker.