[3][4] In 2008, Willamette Week's Amanda Waldroupe described Hobo's as a "chi-chi, predominantly gay establishment" and wrote, "Coming here, you may run into the famous or semi-famous (City Council candidate Ed Garren was spotted), or see escaping sailors emerge from the Shanghai Tunnels—the entrance is in front of the bar—in need of a drink".

He said the space was "primarily a restaurant" with a bar, pool, and pianists performing live, and described the clientele as "an array of Portlanders, many of them looking to get laid".

[7] Christina O'Connor of the Daily Emerald described Hobo's as a "classy and inviting" lounge with candlelit tables and rare access to the tunnels, along with neighboring Old Town Pizza.

[8][9][10] Lonely Planet described Hobo's as a "classy gay-centric restaurant-piano bar" and a "quiet, relaxed place ... good for a romantic dinner or drink", with live music Thursday through Sunday, starting at 7:00 pm.

[11] The restaurant, which Eater Portland's Byron Beck and Conner Reed called "spacious", had an "extensive" dinner menu, serving prime rib, crab cakes, and other steakhouse "favorites", as of 2019.

[13] In 2012, Hobo's was featured on the fourth episode ("Shanghai Tunnels") of the sixth season of the paranormal documentary and reality television series Ghost Adventures.

During the episode, ghost hunters Zak Bagans, Aaron Goodwin, and Nick Groff "delve deep into the dingy Shanghai Tunnels to unearth the spirits that still haunt Hobo's Restaurant ... and collect some compelling visual evidence", as claimed by the Travel Channel.

"[2] In the guide book Moon Portland (2019), Hollyanna McCollom wrote: Had Old Blue Eyes and the rest of the Rat Pack been gay, this is where they would have hung out.