Five O’Clock Steakhouse is the quintessential supper club with unique and exceptional dining deeply rooted in traditions. Even the décor represents a different place and time before all that talk about food trends, snapchatting every dish and innumerable gimmicks. It’s just a place to gather with good food and service. The multicolored lights glow against the warmth of the dark wood, and the music softly bounces off the carpeting while you can enjoy pleasant conversation.
Five O’Clock Steakhouse has been serving the finest steaks and cocktails in this supper-club style of dining since 1946. No wonder they were the Shepherd Express Best of Milwaukee’s first-place restaurant last year for “Best Supper Club” and “Best Steakhouse.” Recently, the Food Network named it the best place for steak in Milwaukee.
At Five O’Clock Steakhouse, the hospitality really does reflect their motto: “You’re only a stranger once.” From the start, I felt as though I was forming a new friendship; the personable and warm bartenders welcome you as you belly up to the bar. You can enjoy a classic cocktail like their signature Old Fashioned or one of their many martinis while mulling over the tantalizing menu. The impeccably dressed server will take your dinner order at the bar and has everything timed perfectly.
Awaiting you at your table is a display of warm sourdough bread with butter and honey, a family style garden salad and the traditional supper-club relish tray. The appetizers and sides are listed first on the dinner menu and include French onion soup ($9), shrimp scampi you can order per piece ($4), crab cakes ($16) and more, along with lovely sides of vegetables. The crab mac-and-cheese dish is large enough to share family style ($17).
All of the steaks come surrounded by butter-sautéed button mushrooms. No matter which cut of steak you choose, they are cooked flawlessly to the requested temperature. The gorgeous charred exterior, juicy interior and bold beef flavor are accentuated by the seasoning. Beef cuts include steer filet mignon in ladies ($39), king ($49), or a specialty cut filet on the bone ($55). The Five O’Clock cut is a hearty porterhouse ($53). My favorite is bone-in rib eye ($48).
For a real show-stopper, try the 32-ounce tomahawk ($75), perfect for sharing. Also on the dinner specials menu is a slow-cooked, Wisconsin lamb osso bucco ($40). The lamb was served with grilled carrots and asparagus, creating a textural contrast and balancing the dish with crunch juxtaposed with the tender, fall-off-the-bone lamb shank. However, I thought that the vegetables could have been cooked just a little longer. There are plenty of choices on a menu that also includes seafood, pork chops and ribs ($35-$140) and some gluten-free options.
I can’t believe I’m admitting that after this hearty meal, we saved room for dessert! The homemade cheesecake, crème brûlée and key lime tart were all divine with a glass of crisp Moscato to finish the perfect meal. You can also complete your experience with one of their “Spirited Ice Cream Drinks,” such as a grasshopper or pink squirrel. Five O’ Clock Steakhouse has music on the weekends in the Alley Cat Lounge and also offers private dining.
