Old Milwaukee, Big Cabs, Zero Apologies
Milwaukee · Steak House · Visit Website ↗
Updated September 2026
Reviewed May 1, 2026 · How we review
RagingWine reviewed Five O'Clock Steakhouse’s wine list and gave it The Reliable — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
Wingman Metrics
Walking into Five O'Clock is like stepping into 1962 — white tablecloths, low lighting, the kind of place where your grandfather ordered a Manhattan and meant it. The wine list follows the same philosophy: no surprises, no apologies, and an unambiguous love letter to California Cabernet. If you came looking for Burgundy or something orange and funky, this is not your room.
The list runs 150-250 bottles and is essentially a California Cab hall of fame — Caymus, Silver Oak, Jordan, Stag's Leap, Duckhorn, Far Niente, and Opus One all make appearances, which is exactly what you'd expect from a steakhouse that has been feeding Milwaukee since 1946. What it lacks is any meaningful breadth: Old World representation is thin, and there's little here for anyone who wants to stray off the beaten Napa path. That said, for what it is — a classic American steakhouse wine list — it delivers the canon reliably, and the 2024 Wine Spectator Award of Excellence confirms the list is at least curated with intention. The ceiling is high (Opus One territory), but the floor is accessible enough that you won't feel trapped.
Twelve to twenty pours by the glass is a respectable spread for a restaurant of this size and style, and the program almost certainly leans heavily on the same California names that anchor the bottle list. Rotation appears static rather than adventurous — don't expect the by-the-glass menu to change with the seasons — but for a steakhouse crowd that wants a dependable Cab with their ribeye, it does the job without drama.
Jordan Cabernet Sauvignon — $40
Jordan consistently punches above its price point — structured, food-friendly, and approachable without sacrificing backbone. In a list where bottles climb fast toward the triple digits, Jordan is the one you order when you want the steakhouse Cab experience without the steakhouse Cab markup anxiety.
Far Niente Chardonnay
Every table in the room is ordering a Cab, which means the Far Niente Chardonnay is sitting quietly underordered. It's a serious, richly textured white that holds its own against a shrimp cocktail or a lobster tail, and in a list this red-heavy, it's genuinely the most interesting detour available.
Opus One
Opus One is the trophy wine on any list — and restaurants know it. At a steakhouse with steep markups across the board, you're paying a significant premium for the name recognition. The wine is good, but the value equation rarely works in your favor here. Save Opus One for a wine shop purchase and put that money toward two better bottles.
Stag's Leap Wine Cellars Cabernet Sauvignon + Dry-aged ribeye
Stag's Leap has the structure to stand up to the fat and char on a dry-aged ribeye without steamrolling it — there's enough elegance in the tannins to complement rather than compete. It's a classic pairing that earns its cliché status by simply working every time.
The Bottom Line
Five O'Clock is a reliable, old-school institution that does exactly what it promises — big steaks, big Cabs, zero fuss — and the Wine Spectator nod confirms the list is more than an afterthought. Just don't come here looking for discovery; come here looking for a great bottle of California Cabernet with a perfect ribeye, and you'll leave happy.
Story Hill · Milwaukee · American, Regional
A compact 12-wine list with glass and bottle prices posted, half-glass portions, and a bottle shop run by the same business. Order the $11 Famille Perrin Côtes du Rhône or the $11 Anjou Chenin Blanc by the glass and confirm current availability, since the menu is linked as 8-22-26. This unrated guide covers the posted beverage menu, not service, storage or markups.
Downtown · Milwaukee · American, Steakhouse, Seafood, Contemporary
A very large list with no by-the-glass section posted: 657 priced wines from $30 to $4,450, and Napa Valley Cabernet Sauvignon is the biggest group at 93 entries. For a starting point, the $50 Jean Marc Martin Haut-Médoc Merlot 2015 is the lowest-priced wine in the "Sommelier's Favorites Reds", and the $70 Thorne & Daughters Rocking Horse White Blend 2023 is the South African pick. Prices carry no unit and the page is undated, so confirm both. This unrated guide covers the posted wine list, not service, storage or markups.
Brady Street · Milwaukee · American
A short, varied list: 35 wines, from Lambrusco and Mourvèdre to Napa Cabernet, with paired numbers from 11 to 15 and a Cruvinet box at 11 to 22. Try the 11 | 43 Pirates del Ebro Tempranillo, or the Selbach Riesling with the scallops, and ask which number is the glass price. This unrated guide covers the posted wine list, not service, storage or markups.
Riverwest · Milwaukee · Pub fare and brewery food
Lakefront is a beer hall with a one-line wine list: three Wollersheim wines at $9. If you want wine, start with the Prairie Fumé alongside the cheese curds and ask about pour size, since the menu does not say. This unrated guide covers the posted drinks selection, not service, storage or markups.
Brady Street · Milwaukee · Italian-American
A friendly, easy list for a pasta-and-pizza room: 19 pours by the glass from $7 to $13, plus bottles from $36 to $90. Start with the $7 Wollersheim Prairie Fumé, or get the $10 Banfi Chianti Superiore with a bowl of Pomodoro, and confirm prices because the page is undated. This unrated guide covers the posted wine list, not service, storage or markups.
Historic Third Ward · Milwaukee · Italian-Mediterranean
A bottle list with Greek, Sicilian and Lebanese bottles alongside Napa Cabernet, and Dom Perignon at $550. Start with the $40 Oenops 'Apla' or the $65 Château Musar 'Jeune', and plan around Wine Wednesday, when the restaurant says select bottles are half price from 5pm to 9pm. Confirm vintages and which bottles qualify before you order. This unrated guide covers the posted wine list, not service, storage or markups.
Washington · Washington · Steak House
A 20-wine by-the-glass list with every pour between $14 and $30, split across four sparkling, six white, two rosé and eight red. With a steak, start with the $26 Clos Duval Napa Valley Cabernet Sauvignon or the $22 Monte Antico Supremus; for the cheapest glass, take the $14 Dr. Loosen Riesling. Pour sizes aren't posted and the page is undated, so confirm today's wines. This unrated guide covers the posted wine list, not service, storage or markups.
Chicago Loop · Chicago · Steak House
A Napa-leaning Cabernet list with a Library & Reserve section that reaches 3,098 and glass pours from $13.99 to $49.99. Start with the $15.99 Broadbent Cabernet by the glass, or the $41.99 Stag's Leap Artemis if the ribeye is on the table, and confirm current availability since the list does not guarantee vintages. This unrated guide covers the posted wine list, not service, storage or markups.
Union Square · San Francisco · Steak House
A glass list that does the steakhouse job: 36 pours, a tidy Napa Cabernet set and prices from $13. Order the $15 Beringer Cabernet with your steak, or the $14 Guado Al Tasso Vermentino if you are starting with seafood, and confirm availability since the page is undated and Morton's says pricing may vary. This unrated guide covers the posted glass list, not service, storage or markups.
One wine list review, one adventure pick, one quick tip, and a personal note. Every week. Under 500 words.
List Variety
Markup
Glassware
Staff
Specials & Deals
Storage & Temp