Bob Hillman, a San Francisco singer/songwriter, is well into the second act of a career that began in the late 1990s, flourished in the early 00s, survived ten years of “real jobs,” and resumed in 2015. Downtown in the Rain, a mostly acoustic, five-song EP featuring guitarist Greg Leisz, was released on November 17, 2023. His two most recent projects are Bob Hillman & Spooky Ghost, a “noise folk” collaboration with former Bowie guitarist Gerry Leonard, and Inside & Terrified, a COVID-era EP featuring Jay Bellerose on drums and David Levita on nylon-string guitar.  

His most recent full-length album was released in April 2019. Some of Us Are Free, Some of Us Are Lost attempts capture the visceral spirit of certain folk and folk-rock masterpieces of the 60s and 70s without specifically referring to their sounds or instrumentation. In hindsight, the only real connection to that era is probably David Crosby’s re-tweet about a song called Cocaine Ruins Everything, which mentions him: “Great song…very very good…well done.”   

That was the second album of Bob’s “comeback” period, which began in 2015 with the release of Lost Soul. Lost Soul is notable for having been produced by songwriting legend Peter Case, who also happens to be one of Bob’s primary inspirations. “I was blown away by Peter’s Blue Guitar album and stalked him after shows starting in the late 80s. He’s given me lots of good advice over the years.” Joseph Arthur also put his stamp on Lost Soul, playing lead guitar and creating the loops that formed the backbone of the record.

Between Lost Soul (2015) and If You Lived Here, You’d Be Home (2003), Bob worked in marketing for consumer packaged goods and internet companies, including Clorox and Intuit. At Clorox, he was in charge of Formula 409 and Glad plastic containers. Clorox – where Bob’s non-traditional background ensured that he would be perceived as an eccentric – was a change of pace from the music industry, where he was regarded as relatively straight-laced. 

In the late 90s and early 00s, Bob released three albums and toured extensively in the United States and Europe. Most notably, he was featured on Suzanne Vega’s entire Songs in Red & Gray Tour – playing venues like the Fillmore Auditorium (San Francisco), The Bottom Line and the Bowery Ballroom (New York), Paradiso (Amsterdam), Shepherd’s Bush Empire (London), and Le Bataclan (Paris) – and landed a slot at the 2002 Newport Folk Festival, where Bob Dylan was also on the bill. During that period, he opened for many prominent artists on the singer/songwriter circuit, including Dan Bern, Todd Snider, Tom Paxton, Dave Alvin, Mary Gauthier, Janis Ian, Ray Wylie Hubbard, and Steve Forbert. 

Bob’s early songs came to the attention of Tommy West, who was Jim Croce’s best friend and producer and worked out of his barn/studio Somewhere in New Jersey. Tommy was Bob’s first musical mentor, financing and producing his first two albums – Playing God (1999) and Welcome to My Century (2001) – teaching him about the music business, and generally playing the role of father figure. Welcome to My Century has probably been Bob’s most successful album, featuring three of his most popular early songs – Valentine’s Day, Bolted Down, and Tolstoy – about the last of which Susan Stamberg once said on NPR: “I’ve never heard of this Mr. Bob Hillman, but that song about War & Peace is enough to make you want to pick up War & Peace and start reading it.” 

Bob got his start in mid-1990s New York City, where he fell in with Jack Hardy’s long-running songwriting group, which met every Monday night in Greenwich Village to eat pasta and share new songs. Bob still relies on arbitrary deadlines and thoughtful feedback to help him write more and better songs: in addition to participating in informal weekly workshops with like-minded artists, he has helped the songwriter Peter Himmelman run an online workshop.