blog header image

A Smile and a Song

Posted on Thursday, October 14th, 2010.

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.



3 Responses to “A Smile and a Song”

To preserve the StoryCorps mission and experience for our readers and participants, comments are subject to the StoryCorps Terms of Service. Comments may be held for moderation or removed if deemed offensive or off-topic. Please do not resubmit your comment if you don't see it right away, it will be approved as soon as possible. Thank you.

  • I have read some articles about him a while back. I admire the way he lives his life. :)

    It’s good to know that there are still people out there that enjoys themselves like this without worrying about money.

    Comment from Long on November 23, 2010 at 12:20 pm - Reply to this Comment
  • It must be real neat to see somebody like that both on and off stage. There’s something about seeing a musician off stage that gives you a better understanding to the lyrical and instrumental meaning to a song. It’s also fun when your the only one who notices a famous musician outside the stage while everyone else has no clue. It shows you who are the devoted fans from those who are on the bandwagon.

    Comment from Paul Flores on November 23, 2010 at 1:55 am - Reply to this Comment
  • I have seen this gentleman playing down in Union sq. many times, and I am so glad he came in to record a story – looking forward to hearing it!
    By the way, I love your project, (I am an oral history and audio nut) and I promote it to friends as often as I can.

    Comment from Eliza on October 14, 2010 at 6:47 pm - Reply to this Comment

Leave a Reply


  • Major Funding Provided By

    CPB Logo
  • National Broadcast Sponsors

    CTCA Logo Ford Logo
  • National Partners

    NPR American Folklife Center at the Library of Congress
  • Charity Navigator Logo