Photos by Andy Argyrakis

More than twenty years may have passed since he ruled the late night television airwaves, but that didn’t stop Arsenio Hall from packing two shows at the always welcoming City Winery. Perhaps that’s because in the ensuring years, the “Coming To America”/ “Harlem Nights” supporting actor also hosted “Star Search,” “The World’s Funniest Moments” and “Greatest Hits,” voiced for “Scooby-Doo! Pirates Ahoy!,” guested on countless programs, briefly revamped “The Arsenio Hall Show,” and of course, won “The Celebrity Apprentice.”

As the familiar voice regains strength with his stand-up footing, there’s no way to forget Arsenio’s tremendous impact in the timeline of late night TV, his ability to stay visible throughout a variety of cultural mediums, and ultimately, keep everyone laughing well into the wee hours.

His latest visit to the Windy City was both a homecoming of sorts (given those burgeoning years spent climbing the area comedy circuit) and marked a return to those very same stand-up roots. As a result, the nearly two-hour evening (including worthwhile local opener Rebecca O’Neal) struck both a nostalgic nerve and the headliner’s commentary on current events, which naturally spent a lengthy segment in politics given his personal relationship with the current president.

But before he got to “the first 100 days,” Hall thanked everyone who instantly greeted him with a “wuff, wuff” for continuing to recognize him, then joked about getting mistaken for Wesley Snipes and Dennis Rodman as of late. After quickly getting comfortable with the rapt crowd, he dropped several swears in rapid succession, establishing a pattern that would unfortunately persist a little too often considering his comedy could’ve usually stood just as tall on cleaner legs (such as his peer Sinbad).

In fact, Hall was the first to address taking a coarser direction following one-time mentor Bill Cosby’s fall from grace, accompanied by a suggestion that fans shouldn’t confuse Dr. Huxtable with “Dr. Fuxtable.” Arsenio also touched on similarities between he and former television boss Donald Trump exclaiming “we both like sports, we both like politics and we both really like his daughter.”

The comic was equal with jabs towards Hillary Clinton, whom he thought campaigned in all the wrong places, and Bernie Sanders, who’s advanced age and “5pm bedtime” was likely a hindrance in getting him on the ballot. Hall continued tearing into the endless array of debate shenanigans, said picking between the two primary candidates was like “having to choose your favorite Menendez brother” and remarked that politics sure have changed a ton since the days when Betsy Ross was simply making the flag.

Additional stories included given his teenage son permission to quote lyrics from Kanye West or Future, as long as he doesn’t talk like the president and his infamous remark about the female anatomy (which Hall promptly turned into a rap). Indeed, no celebrity was off limits, whether it was his pal Prince and the fact that he supposedly never owned a phone or pondering O.J. Simpson’s recent announcement he was planning on becoming a preacher (albeit one who’s “gonna have to preach the nine commandments”).

While the audience was clearly on his side the entire time, Hall seemed to still be dipping his toe back into the waters of live performance and might have benefitted from a little more edge, not in the language department, but in expanding beyond the obvious nature of some material (especially the election). He could’ve also used a stronger ending than comparing the days of skipping vinyl records to the buffering of an internet stream for his son who was having a hard time imagining the archaic concept.

However, it was kind of the celeb to lock back into the present by snapping a couple quick selfies, signing a few autographs and bringing out the opener for a final bow before taking off. As the familiar voice regains strength with his stand-up footing, there’s no way to forget Arsenio’s tremendous impact in the timeline of late night TV, his ability to stay visible throughout a variety of cultural mediums, and ultimately, keep everyone laughing well into the wee hours.

Click here for more Arsenio Hall photos from City Winery.

For additional information on Arsenio Hall, visit ArsenioHall.com.

Upcoming concert highlights at City Winery include the WDCB Jazz Brunch featuring the Mark Colby Quartet (Apr. 30); Ian Maksin (Apr. 30); Eddie Jobson & Marc Bonilla (May 1); Whose Live Anyway? (May 2-3); Eilen Jewell with Leland Sundries (May 4); Don McLean (May 5); Ray Wylie Hubbard (May 6); Paul Thorn Band (May 7); Denny Laine (May 8); Robby Krieger (May 9); Trout Steak Revival with The Railsplitters (May 10); Samantha Fish (May 11); The Blasters with The Delta Bombers (May 12); Robbie Fulks with Nora O’Connor & Scott Ligon (May 13); Story Sessions Brunch (May 14) and Amy Helm & the Handsome Strangers with Connor Kennedy (May 14). For additional details, visit CityWinery.com/Chicago.

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