Mad Men ponies

The Mad Men ponies are nine or more background Earth and/or unicorn ponies designed to resemble some of the cast of the hit AMC drama series Mad Men, including Business Saavy (Don Draper), Peggy Holstein (Peggy Olson), Joan Pommelway (Joan Holloway), Sterling Silver (Roger Sterling), S04E08 Unnamed Earth Mare #, S04E08 Unnamed Earth Stallion #10 , S05E16 Unnamed Earth Stallion # , Micro 08 Unnamed Stallion - Pete Campbell (Pete Campbell), and Micro 08 Unnamed Stallion - Bob Benson (Bob Benson). They are gradually introduced in the IDW comics' Micro-Series Issue #8 and in the episodes Rarity Takes Manehattan and Made in Manehattan, and since around then, most of them are often depicted in episodes taking place in Manehattan. They are unnamed, "Business Saavy", "Peggy Holstein", "Joan Pommelway", and "Sterling Silver" being placeholder names.

Season four
In Rarity Takes Manehattan, "Sterling Silver", Earth pony "Peggy Holstein", and "Business Saavy" are first depicted, "Business" and Earth "Peggy" are depicted working in a Manehattan office, "Joan Pommelway" is first depicted having coffee outside with "Sterling", and S04E08 Unnamed Earth Mare # is first depicted during the song Generosity. In the same episode, S04E08 Unnamed Earth Stallion #10 is first seen, and Earth "Peggy", "Business", "Joan", and "Sterling" are seen waiting in the rain for a cab.

In For Whom the Sweetie Belle Toils, "Business Saavy" is seen in Sweetie Belle's dream as an award nominee.

In Trade Ya!, "Joan Pommelway" and "Sterling Silver" are seen in the crowd as potential traders for Twilight Sparkle's books, "Joan" is seen elsewhere, and Earth pony "Peggy Holstein" is seen.

Earth pony "Peggy Holstein", "Business Saavy", "Sterling Silver", and "Joan Pommelway" appear in the audience in Equestria Games.

"Joan Pommelway" and Earth pony "Peggy Holstein" appear in Twilight's Kingdom - Part 1. "Joan Pommelway" also appears in the recap at the beginning of Twilight's Kingdom - Part 2.

Season five
"Business Saavy", "Joan Pommelway", and Earth pony "Peggy Holstein" make background appearances in Party Pooped.

"Business Saavy", S04E08 Unnamed Earth Mare #, "Sterling Silver", "Joan Pommelway", Earth pony "Peggy Holstein", and S05E16 Unnamed Earth Stallion # make background appearances in Manehattan in Made in Manehattan.

Season six
Earth pony "Peggy Holstein", "Joan Pommelway", "Business Saavy", S05E16 Unnamed Earth Stallion #, S04E08 Unnamed Earth Mare #, and "Sterling Silver" make background appearances in Manehattan in The Gift of the Maud Pie.

"Joan Pommelway", Earth pony "Peggy Holstein", S05E16 Unnamed Earth Stallion #, "Sterling Silver", and "Business Saavy" make background appearances in Manehattan in The Saddle Row Review.

Depiction in comics
At least "Business Saavy", "Sterling Silver", unicorn "Peggy Holstein", Micro 08 Unnamed Stallion - Bob Benson, and Micro 08 Unnamed Stallion - Pete Campbell appear in.

Merchandise
"Joan Pommelway", "Sterling Silver", Earth pony "Peggy Holstein", and "Business Saavy" appear on the season 4 poster.

Quotes
"Watch it!"

- S04E08 Unnamed Earth Mare #, Made in Manehattan