Hillary Russ

Outfits 11-40:

Outfits 41-70:

Outfits 71-100:

Outfits 101-130:

Outfits 131-160:

Outfits 161-200:

Outfits 201-220:

Hillary Meryl Squires grew up on the northwest side of Chicago and always had a love for making people laugh. She is better known by her stage name of Hillary Russ, pronounced like “hilarious”. She now works as a stand-up comedian for Chicago’s Clapper Club.

The Clapper Club is considered one of Chicago’s most high-class comedy clubs. Many rich people go here. In 2021, at 15 years old, Hillary first got a weekend job as a janitor at the club. The club was trying to recover from the recent COVID pandemic, but it was able to survive by posting its content on Patreon. The club’s star comedian was Tony Klintzer. But he would soon be leaving Chicago for an even more upscale club in Miami. The Clapper Club would need a replacement, and fast.

Just before her 18th birthday, Hillary told her boss she would like to advance into the world of comedy. Her boss asked her to write 200 jokes by the end of the week. Staying up nights and taking in all the random ideas and news she could, she produced such a list with only hours to spare. The night after she gave it to her supervisor and went home, he gave it to Klintzer. That night was one of the most memorable that the manager had seen in many years.

And so Hillary achieved her career goal when she was given the role of a comedian at the club. Her jokes entertain some of Chicago’s wealthiest. Whether they are about current headlines, pop culture, or crude humor, there is never a night at the Clapper Club without roaring laughter being heard from outside the building. On many nights, her tips reach $40,000 or more. Hillary also goes to many local parties, either as part of the entertainment or just as a partygoer.

Besides comedy, Hillary is also skilled with the piano. She first played it in the 4th grade and was in the band for one year in high school. Being in her high school band allowed her to get over stage fright, which would be crucial for being a stand-up comedian later. Today, her performances sometimes incorporate some piano music or tricks. The piano she uses is an Uffizi Torino Black grand piano from 1955. Only 109 of these pianos were ever made and they can easily be worth $300,000.

Hillary has golden blonde hair that transitions quickly to black at the roots. Her eyes are somewhere between green and brown. She has rosy light skin and her cheeks have faint freckles. Hillary tends to perform in a gold-colored shiny dress with a plunging neckline. There is no actual gold in the dress. Her dress is accompanied with a black bowtie on a choker. She can spin the bow tie or squirt water from it by pressing hidden buttons under the fabric of her dress. She also paints her nails black and gold to match her trademark outfit and uses a lot of pink lipstick. Her shoes are a pearl purple color. Her colossal wardrobe of over a hundred dresses and other outfits is spread across multiple closets on her yacht, the Capybara; her parents’ house; and the backstage area of the Clapper Club. 

Hillary lives not in a house, but on a yacht called the M.Y. Capybara. The yacht is homeported on Lake Michigan in Chicago and is packed with many features. It is 118 feet in length and has a total of four decks. The flybridge is the top deck, containing a social area and the secondary helm. Below this is the main deck. This contains the main helm at the front of the superstructure, with a corridor bypassing the owner’s cabin and going to the dining room. The forecastle atop the main deck contains a hot tub. Hillary’s cabin is between the main bridge and dining room, inside which are her bed, dresser, desk, and 66 inch TV with her stereo. On her desk is her business laptop and by the bed is the enclosure for her bearded dragon Bandit. Aft of this is the dining room, with the galley further aft. On the lower two decks, there are also six guest cabins and crew facilities along with the engine room. Despite the yacht’s name, it looks nothing like an actual capybara.

Hillary does not fully own the Capybara; two other people have 17.5% stakes in the vessel. They are the tennis player Lottie Vic (whose cabin is the one on the port bow on the guest deck) and a third, anonymous multimillionaire. But Hillary has 65% ownership and uses the yacht as her primary residence. Due to her career and residence, her wardrobe is mostly dresses and swimsuits, respectively. While Hillary likes to go yachting on Lake Michigan, she doesn’t like all the hard work that goes into it, especially when fixing someone else’s mistakes or problems.

Her stereo is a Bertram R-2440 20th Anniversary Edition that is connected to her TV through an optical cable. The unit has a phonograph and dual cassette player, but the best feature is its 25-disc changer made of five 5-disc trays. The R-2440 first came out in 2003 and was produced until 2011. In 2023, Bertram restarted production to celebrate the model’s 20th anniversary. Hillary uses her R-2440 with a Bertram C9B tuner/Bluetooth transmitter combo. It can receive shortwave, AM, and FM transmissions and there is a small time zone world map engraved on the front. With the press of the Bluetooth button, Hillary can play anything she wants from another device. There is a shortwave station called Radio Free Library that Hillary listens to. It is based in Ciudad Victoria, Tamaulipas, Mexico but conducts broadcasts in English, Spanish, and Vietnamese. This station broadcasts readings of books that have been banned in schools in many American states, along with information about how to get and use a shortwave radio. She also knows about an unnamed pirate shortwave station from Guyana that broadcasts obscure pop music, and of course the many local AM and FM stations in Chicago. Hillary’s speakers are two 1980s-era K&R wood finish speakers.

The aft right guest cabin of the Capybara serves as pretty much a second owner’s cabin for Hillary. Inside, she keeps any clothes she can’t fit in the closet of the owner’s cabin along with her gaming PC on the small desk. Her rig is a Catalista 22-16, an Italian-designed and crafted gaming PC with a Sewadi CPU and other internals made by Intel and Nvidia. The 22 in the model name means the custom-made Sewadi CPU has 22 cores (and 44 threads). The 16 comes from the Intel Arc A770 GPU which has 16 GB of memory. The Catalista 22-16 has 20 GB of RAM with extra DIMM slots for two more sticks. The case is shaped like an irregular hexagon and sits on a stand for better airflow. On the frontmost corner is a customizable mini screen. An Italian flag badge serves as the power button. Hillary has given her rig a Legacycurve monitor, a modern curved monitor with a transparent disc drive built into the base. The screen itself has 5K ultrawide resolution and a refresh rate of 140Hz. Final Fantasy XVI, Minecraft, and the Spider-Man series are Hillary’s favorite games. Cuphead is also installed on her PC but she has never beaten that game. She hopes to preorder Grand Theft Auto VI the literal moment it becomes available.

The Capybara has one full time non-human inhabitant. That is Bandit, her pet bearded dragon. He lives in his enclosure in Hillary’s cabin on the yacht by the bed. Hillary feeds him crickets, superworms and greens daily at the same time she eats her own lunch. She has a colony of superworms under the TV but usually buys only a few crickets at a time because of them needing so much maintenance it would be like having a second pet. Bandit also loves to listen to music from Hillary’s stereo and take walks on deck or on land.

Hillary also has half ownership of a jet, an Embraer Phenom 100. This is a very light jet, the smallest and cheapest category of private jets. It has seating for four passengers, a small snack area, and a toilet. On the outside is Helvetica Aqua Aero livery. The jet has the FAA registration number N885BV. Brad and Velma Webb are the other owners of the plane, with Velma being Hillary’s pilot. They owned the jet in full until Brad decided to split the plane‘s ownership into two shares and sell one to help buy his son Kyle a house. Hillary herself has some knowledge of basic airplane controls, but she cannot use the navigation system or radio to save her life. The Webb family have a hangar at Chicago Executive Airport and Kyle went to the same school as Hillary, albeit six grades ahead.

For land transport, Hillary owns or has access to a number of expensive cars. To be driven to the Clapper Club each night and for public events, she uses a Rolls-Royce Phantom VIII. This car is painted gold and black with Clapper Club decals. The Club has a fleet of four Rolls Phantoms that it uses to transport the owners, managers, comedians, and the highest tier VIP customers. While this Rolls is technically Club property, Hillary does own a teal Mercedes-Benz AMG GT-S and even a Pagani Huayra with a similar decal job to the Rolls that takes her to work. Both of her own cars are kept at her parents’ house, where they have displaced her dad’s red 1999 Volvo station wagon that now sits outside the garage. Because Hillary’s Pagani is worth AT LEAST $3.5 million, she always takes her shoes off before getting in and never brings Bandit with her in this car. She would like to someday own an Ajlani Drakuma or Bugatti Centodieci.

Hillary is mixed-race, being of British and Tahitian descent. Her father Tony Squires is a car salesman and her mother Susan is a dog trainer. They still live in Hillary’s childhood home, an average house in the Jefferson Park area of Chicago. 

She has a younger sister named Sloane. Three years younger than Hillary, her favorite pastime is searching for lost media, and her favorite type of lost media is music. Besides trying to find lost media, Sloane has also been on the Capybara and developed a liking to yachting on Lake Michigan. Their father is now worried about how he will afford boats for both of his daughters. Sloane has a pet hedgehog named Muffin who lives in her room. Hillary interacts and plays with him every time she visits her parents’ house.

Hillary has a maternal aunt named Dora, but she is a miscreant and estranged from the Squires family. She was suspended from school many times going as far back as when she was 8 years old, and was expelled from two different schools. Aunt Dora’s first arrest was at the age of 20 in 2004 for HIPAA violations and forgery. She was working at a dental clinic and frequently gossiped about patients. One patient reported her to the HHS. During the investigation, the police also found that she had used a stolen and altered high school diploma to to get her job at the clinic. She served a sentence of 2 years and 4 months for these crimes. Since then, Aunt Dora has been arrested twice more, first for DUI, and then for once again trying to steal someone’s identity to leave behind her criminal record and get a desirable job. Her daughter - and Hillary’s cousin -  is Jasmine. She is 11 years old and acts as a mediator between her mom and the rest of the family.

For just over one week in March 2024, Hillary was romantically involved with UChicago football player Merlin Spencer. He posted a picture on his Instagram showing him giving Hillary some Maroons merch. But the relationship didn’t last because the entire time, she felt Merlin was using her for her money and attractiveness, rather than genuine romance. She still has one of his #59 jerseys.