Winfrey welcomed Lohan onto her series Oprah's Next Chapter for the Canyons actress's first interview since spending 90 days in rehab to resolve her reckless driving case.
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The two discussed Lohan's long history of legal troubles, with the actress admitting that her first DUI arrest years ago led to no significant changes her behaviour.
"You would think in that situation, someone would be like 'Holy s**t, I need to check myself''," Lohan recalled.
She went on to say: "It's the definition of insanity, doing the same thing over and over again."
Lohan also disclosed to Winfrey that she had used cocaine 10 to 15 times in her life.
"I really haven't done it more than 10 to 15 times," she revealed to Oprah. "Of course I said three to four [in the past]! I was terrified and humiliated. No, it never felt good the next day. It allowed me to drink more. It went hand in hand with drinking."
The actress credited her recent stay at the Cliffside centre in rehab with convincing her to give up ADHD drug Adderall, which she had been taken for quite some time.
Lohan then stressed to Winfrey that her time at Cliffside allowed her to "feel whole" for the time in years.
"I have such a desire to want to keep this feeling and stay that way, and I'm willing to do whatever it takes," she said, adding: "I really want to be on set. That feeds me."
She also commented: "I have to regain the trust of people in my career that have their doubts, and I fully respect that. I hate that label and that title [of being a troubled child star]. That's not what I ever aspired to be. That's not what I want in my life.
"As long as I stay honest with myself and just do the work that I'm willing to do and have been willing to do and am doing, then there's nothing that can stand in my way of that. I'm my own worst enemy, and I know that and I've been."
The actress also discussed her difficult childhood with parents Michael Lohan and Dina Lohan, but suggested that their squabbles were not the cause of her own personal problems.
Winfrey closed the chat by expressing support for Lohan to rebuild her career, saying: "I want you to win."
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Lohan sat for the exclusive interview as part of an overall deal with OWN, which is reportedly worth $2 million (£1.3 million).
The Liz & Dick actress is also currently filming a docu-series for the cable network.
Oprah's Next Chapter airs on Sundays on OWN.
Photo Gallery: Lindsay Lohan life in pictures
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