Walk into Five O'Clock Steakhouse and the atmosphere hits immediately—dark wood paneling, red leather banquettes, and the soft glow of table lamps creating pockets of intimacy throughout the dining room. A lounge singer's voice drifts from the bar area, mixing with the clink of cocktail glasses and the low hum of conversation. This is supper club theater at its most dramatic, somewhere between nostalgic charm and film noir setting.

The ritual begins properly when your server sets down the rectangular metal relish tray, its compartments filled with pickled vegetables, followed by warm bread and butter. Watch the tableside salad preparation unfold—crisp greens tossed with practiced precision while you sip an Old Fashioned from a faceted rocks glass. These opening acts set expectations high, and when it comes to the steaks, the kitchen largely delivers.

The rib eye arrives on an oval platter, its surface deeply charred and glistening. Cut into the meat and pink perfection reveals itself, each bite carrying that unique flavor profile that sets Five O'Clock apart from the competition. The bone-in filet proves equally impressive, so tender it barely requires a knife. Even the New York strip, often an afterthought at lesser establishments, shows the kitchen's mastery of heat and timing.

Seafood tells a different story. While the walleye special can shine when available, arriving golden and flaky, the regular menu's limited fish options struggle to match the beef's excellence. Shrimp scampi ranges from spot-on to merely adequate, depending on the night. The fish fry satisfies without inspiring, competent but unremarkable in a state known for Friday night fish.

Service flows with the precision of a well-rehearsed performance. Servers like Annie transform first visits into memorable experiences, their genuine warmth making the hefty check easier to swallow. They navigate the dining room with practiced ease, timing courses perfectly and ensuring glasses never empty.

The bar program shows similar inconsistency. That Brandy Alexander arrives picture-perfect in its balloon goblet, creamy and balanced. The Old Fashioneds vary wildly—some nights they're transcendent, others merely serviceable. For a place trading on liquid nostalgia, the mixed results disappoint.

Sides and extras reveal where corners get cut. Asparagus appears barely warmed, lacking butter or seasoning despite its premium price. Mashed potatoes and green beans perform adequately without distinction. The calamari appetizer hits the right notes, but desserts swing from sublime tiramisu to portions that vary inexplicably from plate to plate.

Five O'Clock Steakhouse remains a Milwaukee area institution worth experiencing, especially for those spectacular steaks that justify the reputation. The atmosphere delivers drama and nostalgia in equal measure, service rarely falters, and when everything clicks, you understand why regulars return despite bills that can easily top $400 for three. Yet for a place charging premium prices, the inconsistencies in cocktails, seafood, and sides suggest opportunities to elevate the entire experience to match those exceptional steaks.