When I first saw Jerry McLilly approach the San Francisco StoryBooth, I felt that I recognized him from someplace in the past. As he began to tell his story, it finally hit me: He was that remarkable and unforgettable crooner in the dapper suit that I had heard so many times over the years in downtown San Francisco, singing his signature numbers, “When You’re Smiling” and “I Left My Heart in San Francisco.”
Also known as Mr. Smiley, Jerry sang for most of two decades in front of the old Emporium store, before and after it closed (the facade still stands as the entrance to Bloomingdales). We were fortunate that this day in August he brought some songs, his engaging smile and his story to share with us.
While at high school in Detroit, Jerry met Jackie Wilson, who later went on to become a major rhythm and blues star with “Lonely Teardrops” and “Reet Petite.” Jerry was hired for $175 a week as Wilson’s valet and chauffeur when they began a tour of the “Chitlin Circuit” – D.C, Philadelphia, Los Angeles, The Fillmore in San Francisco, and the Apollo in Harlem. Jerry rehearsed with his mentor and role model and began his professional singing career. After some years on the road with Wilson, he performed with a later version of The Ink Spots vocal group in venues around the world.
Famed newspaper columnist Herb Caen advised Jerry to take his solo act to the streets of San Francisco, first Market Street, Fisherman’s Wharf and later Union Square, where Jerry now can be seen and heard outside Saks Fifth Avenue at Powell and Post. Hailed as an Ambassador of The City by former San Francisco Mayor Willie Brown, over his 45 years of performing Jerry has been featured on local television stations and newspapers and, in 2006, made a cameo appearance in the film, “The Pursuit of Happyness.”
Troubled with a bad knee, Jerry “soldiers on,” keeping to a weekday schedule of performing from 9 am til 2 pm.
Living in a city can lead us to a calloused indifference. We put on the blinders and tune out too much of the world. Jerry McLilly is the antidote to the woes of a sometimes heartless city. With his radiant charm, Jerry calms a pedestrian’s fear of being accosted in the street by a stranger. He gives a passerby a smile and a song and, in return, he gets a smile and some money. Jerry is all about feeling good and passing that vibe on.
Jerry McLilly came to StoryCorps through our outreach relationship with Community Housing Partnership.