The 17 Best Secretaries in Pop Culture

By Bonnie Stiernberg  |  May 11, 2011 | 7:37am
TV Lists

10. Miss Blankenship, Mad Men (Randee Heller)
Her time on Mad Men was brief, but Miss Blankenship was a lifer. She spent decades in an office environment, and — brought on to break Don’s streak of sleeping with his secretaries — she ultimately met her demise at her desk.

9. Jonathan, 30 Rock (Maulik Pancholy)
Jonathan’s affection for his boss is creepy, hilarious and second to none. He’s always looking out for Jack, declaring, “Popes and princes count their Donaghy time in seconds!” We should all be so lucky.

8. April Ludgate, Parks & Recreation (Aubrey Plaza)
April’s the ideal secretary for Ron Swanson: She never answers the phone, and memos go straight into the trash. Together, they’re an unstoppable team of misanthropes. Watch out for March 31, though. It’ll catch up to you.

7. Lee Holloway, Secretary (Maggie Gyllenhaal)
After taking a job with lawyer/sadomasochist Edward (James Spader), shy, troubled Lee stops cutting herself, gains confidence and eventually leaves with a husband (and probably a great reference).

6. Kitty Sanchez, Arrested Development (Judy Greer)
Arrested Development’s premature cancellation is one of TV’s greatest crimes, and George Sr.’s fiercely loyal assistant is one of the many reasons we should all be kicking ourselves for not tuning in more frequently while the show was still on the air. Say goodbye to these, America!

5. Grace, Ferris Bueller’s Day Off (Edie McClug)
The sportos, motorheads, geeks and the rest of them may think that Ferris is a righteous dude, but we think Principal Rooney’s right-hand gal is pretty great herself.

4. Waylon Smithers, The Simpsons (Harry Shearer)
Technically Smithers is more of a live-in assistant to Mr. Burns, but he’s certainly got a lot in common with some of the others on this list, whether it’s his undying affection for his boss or the dysfunctional relationship they share. Working for someone as evil as Burns can be tough, so it’s no wonder he gets caught in dreamland once in a while.

3. Moneypenny, James Bond movies (Lois Maxwell)
Poor Moneypenny. As M’s secretary, she’s often left with the task of tracking down 007, but she never gets to enjoy any of the (ahem) perks of being a Bond girl. Can’t blame a girl for trying, though. Over 20 movies’ worth of flirting? That’s dedication.

2. Pam Beesley, The Office (Jenna Fischer)
Long before she was a married office administrator with a baby, Pam was the sad-sack receptionist we were all rooting for. We cringed as her dreams of becoming an artist were dashed, and we cheered when she and Jim finally got together. It takes a special kind of someone to deal with Michael Scott’s ridiculousness; Pam earned her happy ending.

1. Peggy Olson, Mad Men (Elisabeth Moss)
When Peggy first started at Sterling Cooper, she was a wide-eyed secretary being schooled by Joan on how to lure a man, but in four seasons, she’s evolved into a confident copywriter. She’s gone from timidly referring to Don as “Mr. Draper” to holding her own in shouting matches with him, all during a time period when women in the workplace were a rarity. Can someone get Elisabeth Moss an Emmy already?

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