Jazz Age Jubilee

• Commissioner Warren JusticeShow detailsChicago's police commissioner presents himself as the last honest man in a corrupt system. Publicly, he's waging a war against bootleggers and speakeasies, but privately, he's known to enjoy the occasional illegal drink. His presence at the club opening raises eyebrows—is it an official investigation or personal pleasure? Recently, he's been investigating corruption within his own department, making him unpopular with certain officers. He seems unusually interested in several of the guests tonight, taking notes in a small notebook he keeps in his breast pocket.
• Detective Oscar 'Oz' MartinezShow detailsA rising star in Chicago's police department, Detective Martinez has built his reputation on being incorruptible in a force known for taking bribes. He's officially off-duty tonight but seems to be conducting unofficial surveillance. His presence makes several guests noticeably uncomfortable, particularly those with connections to the city's criminal organizations. Recently, he's been investigating a series of art and jewelry thefts at high-society events—exactly the kind of gathering 'The Velvet Note' opening represents. He's been quietly questioning the staff throughout the evening while pretending to simply enjoy the music.
• Dr. Ellington BlackwoodShow detailsA prominent physician who treats Chicago's elite, Dr. Blackwood is known for his discretion regarding his patients' ailments—particularly those resulting from illegal alcohol consumption. He's also rumored to help gangsters injured in turf wars who can't go to hospitals. Educated at Harvard, he returned to Chicago to serve his community but became entangled with the city's criminal element out of financial necessity. Tonight, he seems unusually interested in the club's back rooms and has been observed taking frequent sips from a flask that doesn't appear to contain alcohol.
• Isabella 'Bella Donna' BelmontShow detailsA famous silent film actress whose star is fading with the advent of 'talkies' — her stage-trained voice, magnificent in a theatre, doesn't sit well on the new sound technology. Known for playing femme fatale roles, she carries herself the same way off camera. Rumors swirl about a husband who walked off a yacht and never came back, and about the inherited fortune of unclear origin that has been keeping her household afloat ever since. She's been arguing with her agent throughout the evening about a role she desperately wants. The diamonds she wears tonight are rumored to be gifts from various admirers, some of whom are also present at the club opening.
• Melody BluenoteShow detailsThe headline performer at 'The Velvet Note,' Melody has a voice that can break hearts and mend them in the same song. Rising from poverty to become one of Chicago's most beloved jazz singers, she's finally achieved the fame she's always craved. However, success hasn't erased her ambition—she wants to own her own club someday. Known for her perfectionism and fiery temperament, she's been particularly on edge tonight, snapping at the band and demanding changes to the lighting just minutes before the show.
• Richie 'The Finger' GoldwynShow detailsA former speakeasy operator who's gone legitimate with the opening of 'The Velvet Note.' Richie has paid his way out of trouble more than once and is now trying to go fully legit, trading the back-room ledgers and palm-greased patrolmen for a city license and a respectable opening night. He's quick-tempered, watchful, and known for an iron memory for slights. The club represents everything he's worked for, but he's made many enemies along the way. Tonight should be his crowning achievement, but he seems unusually tense.
• Ruby DiamondShow detailsA cigarette girl at 'The Velvet Note' with dreams far bigger than her tray of cigars and cigarettes. Ruby has a photographic memory and remembers every face, name, and conversation she overhears—making her a valuable source of information in Chicago's underworld. She's working her way through law school by day and selling cigarettes by night, a fact known to very few. Tonight, she seems distracted, having dropped her tray twice already. She's been seen passing notes between certain guests, though she claims they're just cigarette orders.
• Sammy 'Fast Fingers' KeysShow detailsThe most talented jazz pianist in Chicago, Sammy's playing is legendary for its speed and emotion. Born into poverty, he taught himself to play on discarded pianos and worked his way up through the city's jazz clubs. Despite his current success, he remains bitter about the years of exploitation by club owners who paid him a fraction of what white musicians earned. He's particularly resentful of Richie Goldwyn, who once owned a club where Sammy played for tips. Tonight marks the debut of his new composition, which he claims will revolutionize jazz.
• Senator William 'Big Bill' SterlingShow detailsA powerful state senator with presidential ambitions, Sterling publicly supports prohibition while privately indulging in the finest illegal spirits. His political career has been built on 'family values' and 'law and order' platforms, making his presence at a speakeasy potentially scandalous. He's been meeting with various guests throughout the evening, engaging in hushed conversations that stop when others approach. Recently, he's been pushing legislation that would increase penalties for prohibition violations, which seems at odds with his attendance tonight.
• Sophia SterlingShow detailsThe elegant wife of Senator Sterling comes from old money and older secrets. Behind her perfect smile and impeccable social graces lies a sharp intelligence and a will of iron. While she plays the role of the supportive political wife in public, those who know her well understand that she's the true political strategist in the family. She's been unusually interested in Melody Bluenote tonight, watching her performances with an intensity that goes beyond appreciation for music. Her jewelry collection, particularly the diamond and sapphire necklace she wears tonight, is famous throughout Chicago society.
• Tommy 'The Ghost' HollowShow detailsRichie Goldwyn's right-hand man and head of security for 'The Velvet Note.' A former private security operative, Tommy earned his nickname by appearing and disappearing without warning. He's fiercely loyal to Richie, who he saved during an armed robbery years ago. Despite his intimidating presence, Tommy is surprisingly well-read and quietly philosophical, more apt to defuse a situation with a quiet word than a raised voice. He's been unusually nervous tonight, constantly checking the club's entrances and exits. When asked about his concerns, he dismisses them as 'professional paranoia.' He carries a concealed pistol, which is common knowledge among the club's regular patrons.
• Vivian GoldsmithShow detailsSociety columnist for the Chicago Tribune and daughter of one of the city's wealthiest families. Vivian uses her social status to gain access to exclusive events, then publishes the scandals she uncovers. Her column has ruined reputations and careers, but her family connections have protected her from retaliation. Tonight, she's been unusually quiet, observing more than participating in conversations. She carries an expensive camera and has been taking photographs throughout the evening, despite some guests' obvious discomfort.

Up to 32 guests in total · portraits are AI-generated