After years of odd jobs and countless gigs at weddings and bar mitzvahs, Jeff Oster, 53, is enjoying success at the top of the charts. He just finished recording his third album, and his first, Released, won the Zone Music Reporter's Album of the Year award in the New Age category. His second, True, did the same.
Born in southern Illinois, Oster lived all over the United States—Virginia, Chicago, Massachusetts, Rhode Island, Oregon, New York and Los Angeles—before settling with his family, wife Toni and two children, in Alameda in 1998.
Oster often plays his flugelhorn at Alameda venues such as the New Zealander and Rooster's Roadhouse. He also jams with the Bob Claire Orchestra, a 12-member Motown band.
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What do you like about Alameda? I've lived in California since 1979 and Alameda's the only place I've been that's truly a neighborhood. I've lived in places down in southern California where maybe I've known one neighbor after living there for two or three years. Here, it's incredible how interconnected how everybody is. It's a great place to raise a family. It's safe. You can't drive faster than 25 mph. And it's really close to the city so it's easy to get there.
How did you get into music? I started playing trumpet in school when I was 8. I took lessons and was in the band. When I moved to Florida, I had an inspirational band director and I was in the concert band and marching band. We went to Europe and the state band competitions. For me, it brought music to a different level. Then when I was in college, I auditioned with Ray Charles in Los Angeles. I didn't get the gig but I decided to move to Los Angeles in 1979 to be the next Herb Alpert.
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How would you describe your musical style? They put me in New Age. The new music I'm working on is a little bit more down-tempo chill music. I like to tell people it's like Miles [Davis] meets Enya.
When do you write? Most of my writing happens in the evening. Then I'll take a week off and record.
You've held a variety of jobs. Tell me about some of them. I've done everything from loading liquor on trucks at booze warehouses to selling office supplies. I did stand-up comedy for about four years. I was an off-and-on limo driver for about seven years. When I was driving, I used to pitch my songs to people in the back.
Sort of a captive audience? I used to lock the doors and say "How'd you like to hear my new song?"
How were your tips? Pretty good. Actually I got into ASCAP [The American Society of Composers, Authors and Publishers] that way and met Mel Tillis who published one of my songs.
What's the strangest job you've had? Driving Andy Williams' dog from the private jet to his house.
No tips from that one? No tips.
Did the dog like your music? It didn't howl ... although it did hang out from the window!
And then you became a financial planner? In 1986, one of my friends said, 'You're good on the phone. You should be a financial planner.' I said 'Dude, I never took a finance class in my life. No way.' So he comes over one day with a big stack of material for me to study for my stock broker license and so I started studying about stocks and bonds. I'd take this class from 8 in the morning until 5 at night. Then I'd play a gig from 9 at night until 2 in the morning. During fifteen minute breaks at the club, I'd study for the exam.
I just got tired of being poor. And I decided if I wanted to do original music—especially in Los Angeles where you have to pay other musicians to play with you—I had to make enough money in my day job as a financial planner to do it, to hire the people I wanted to hire and play where I wanted to play. It took from 1987 to 2003 for me to do that.
It took you a long time to become successful as a musician. What advice would you give to young performers? Persistence pays off. Every musician has their own voice. Sometimes there's a lot of pressure to think about what's hot today. I spent a lot of time trying to write songs in a particular style that was popular. And I didn't really find success until I actually started to do songs that were about what I truly loved.
To hear some of Oster's music, click here.
