By the time she was 39, she had been charged with prostitution, drug possession, attempted burglary and assault with a deadly weapon. These days, however, she is more known to the police for her actions on the other side of the bars.
Five days a week, Lamarr runs Choices, a program at the Maguire Correctional Facility in Redwood City that teaches nearly 200 inmates "social survival skills" through parenting classes, math lessons, GED preparation and a variety of workshops.
"She runs a very tight ship. She probably does more yelling at inmates than we do," Correctional Officer Michael Shanks said with a chuckle.
At a recent workshop, she asked returnees to share what brought them back to the jail and the behavior that might have fueled this return, then asked other inmates to suggest ways to prevent these relapses. Just focusing on your drug addiction is not going to make your life successful, she emphasized to them -- you have to change your way of thinking and being to break these old patterns of behavior.
A lot of the inmates in the program are there because of drug-related offenses, Lamarr explained, but these crimes aren't just petty theft or drug possession.
"This is a critical thing that people need to understand," she said. "Drug-related crimes can range anywhere from stealing some meat out of Safeway all the way to attempted murder or murder if you get into a bad situation, because that whole scene, that whole life, that whole environment is horrible."
Lamarr was raised in that environment. Her mother was an alcoholic, so she was mostly raised by her grandmother. At 15, she got pregnant and entered a brief marriage that was wracked with domestic violence. By her early 20s, she had five children, one of whom died months after birth. During that whole time, she was hooked on heroin.
"When you're addicted, you don't realize that you are messed up 100 percent," she said. "I've run in the streets, lived in hotels, lived in cars, I've hooked up with 'Freddy Kreugers,' men that were violent and crazy, men that were on drugs and going in and out of prison. That's the way I was."
In 1989, Lamarr was sitting in the Solano County jail, prepared to go to prison for eight to nine years for first-degree burglary. A correctional officer suggested she contact the Delancey Street Foundation, an organization based in San Francisco dedicated to turning around the lives of those who "have hit bottom," improving their job and social skills and aiding their reintegration into society. Lamarr's letter led to an interview with representatives of the foundation.
At that point, Lamarr recalled, "I didn't even care. I was sick, I was kicking drugs. Two women came to the jail and interviewed me. One of the women was named Charlotte Harper. I was sitting on the side of the plastic or glass and I had a mohawk and no front teeth.
"But I thank God she saw past all of that and I was accepted to Delancey Street," she continued. "It was the single greatest thing that happened to me in my life."
Because of this, the judge modified her sentence so she could go to Delancey Street. The minimum commitment there is two years, but Lamarr stayed for five, and now she sits on the board of directors.
She credits her rehabilitation to two women in particular, Mimi Silbert, the president and CEO of Delancey Street, and Teri DeLane, a lifetime board member. They "kicked her butt" and made her the person she is today, Lamarr said.
After graduating from Delancey Street, she moved to Oakland and ran a residential sober-living hotel. In 1994, DeLane contacted Lamarr and asked her to help run a program starting in the Redwood City jail. San Mateo County Supervisor Rose Jacobs Gibson, then-Sheriff Don Horsley and others had wanted to start a program for inmates.
"They wanted people to be productive in jail instead of being warehoused," said Lamarr, adding that the Choices program is a "Delancey Street replication." She credits its success to a great collaboration among the Sheriff's Office, Correctional Health Services, the Board of Supervisors, the county judicial system, the probation department, and of course, the community.
She also praised Horsley's successor, Sheriff Greg Munks, for believing in Choices and making sure the program and others similar to it stayed active despite budget cuts.
"She teaches on a daily basis: 'Get up, work hard, stop making excuses and give it back to someone else,'" said DeLane, who has since retired from the program. "She does that very well with a lot of tough love."
Michael Candelaria, a Choices counselor, agrees with the effectiveness of Lamarr's tough love. "When she talks, they listen. She has a very deep insight and can read people really well," Candelaria said.
And the inmates themselves vouch for her.
"Shirley is the mother I never had," said inmate Jake, 30, who did not disclose his last name. He has been in the program for 13 months. "She goes out of her way to show empathy I never got as a child."
"Ms. Shirley is a lifesaver," said Raj, 28, another inmate in the program. "She opened my mind to different ways of thinking, and now I think about how my actions can hurt other people."
In 2006, Lamarr was inducted into the San Mateo County Women's Hall of Fame for her work in Choices and turning her life around. But she finds more satisfaction in seeing others' lives changed.
During an interview last week for this article, a young server at a local cafe stopped Lamarr and asked for her name. When Lamarr confirmed who she was, the server hugged and thanked Lamarr for helping her male companion who had been in the program.
As the server left, Lamarr smiled and said, "This is what I live for."