Woodlawn Tap

Chicago, Illinois

Field Note

Chicago dive bar aficionados have long known of Woodlawn Tap, affectionately referred to as Jimmy’s in honor of original owner and bartender Jimmy Wilson. The dive bar’s south side Hyde Park location may be slightly off the beaten path for some Chicago visitors, but a history that dates back to 1948 and the bar’s beloved neighborhood status provide ample reason to make the trip.

Wilson opened Woodlawn Tap in 1948 and operated the bar until passing away in 1999, a period of longevity legendary among Chicago dive bar fans and Hyde Park residents. The space served as a restaurant as early as 1926 before stints as ice cream delivery hub and precursor bar Little Tom’s Place. Wilson purchased the space in 1948 with partner Michael Filz, the business at that time a combination package store (liquor store) and bar. In relation to today’s three-room Woodlawn Tap layout, what was once the liquor store is now the middle room and main or ‘first’ room has always been home to the bar.

After a minor claimed to have been served beer by Wilson in 1952, the bar’s liquor license was revoked for a short period of time until a local judge and community leaders successfully called for the restoration of the license. Woodlawn Tap’s proximity to the University of Chicago will forever link the two institutions, Woodlawn Tap earning the reputation as a “square” bar in 1958 due to a clientele that included students both studying and playing chess.

At that time, Wilson expanded into a third room, dubbed the University Room, requiring visitors to show a valid student ID to access this new space reserved only for local students. The practice persisted until 1967 when this westernmost room was opened to all visitors and augmented to include the stage still used today. 55th Street in Hyde Park, supported by University of Chicago students, was once home to dozens of bars like Woodlawn Tap, but their numbers dwindled over the next few decades, bottoming out during the 1980s when Woodlawn Tap was one of only a handful of businesses left intact.

Wilson persisted despite the relative downturn of the area, ultimately riding the wave of gentrification and revitalization back to Hyde Park’s current vibrant status. As an example of the community’s support of Wilson and Woodlawn Tap, the Illinois state legislature passed a resolution honoring Wilson and the University of Chicago named him an honorary postdoctoral alumnus.

When Wilson passed away in 1999, Woodlawn Tap again lost its liquor license, this time thanks to a complaint from a University of Chicago graduate student (et tu?) who claimed the bar was within 100 feet of a school, violating local ordinance. Thanks in part to the testimony of the reverend of the church operating the school in question, the bar’s liquor license was restored when it was argued Woodlawn Tap was within 100 feet of not a school but a church parking lot, invalidating the complaint. New owners Bill & Jim Callahan successfully navigated the legal challenge and once again proved the community’s love affair with Woodlawn Tap.

The bar was sold again in 2021 to current owner Matt Martell, a longtime bartender at Woodlawn Tap dating back to the 1990s, ensuring a commitment to keeping the space as it always has been. The tin roof found inside Woodlawn Tap is original, as are the swinging doors found between a pair of the bar’s rooms. Basic food is served here as it always has been, the Swiss burger a particularly popular item within a menu that includes hot dogs, sausages and a handful of sandwich options.

Naturally, Woodlawn Tap is cash only as it always has been and no Budweiser can be found here, the symptom of a disagreement Wilson had with a local Budweiser distributor. After Budweiser refused a volume-based discount for Woodlawn Tap, Wilson vowed never to sell Budweiser again. When the local distributor sent over free cases to smooth things over, Wilson placed them on the front step to be given away free rather than sell the product inside Woodlawn Tap.

So revered is Woodlawn Tap that Barack Obamas is said to have visited, as have long strings of celebrities and local artists including Bob Newhart and Dylan Thomas. Though not displayed for preservation purposes, Wilson kept a ‘guest book’ of sorts during the 1950s, asking anyone Wilson deemed interesting to sign the book for posterity.