The chat show queen - who recently interviewed the 'Diamonds' singer on her show 'Oprah's Next Chapter' about her relationship with the R&B singer who assaulted her in 2009 - praised the pop princess for being able to forgive him.
She told entertainment series 'Extra': ''You know what I loved about that interview is that she came with a big, wide open heart. She was in the space of forgiveness. And that she learned a lesson, that she was repeating with Chris Brown exactly what she needed to learn from her father.''
During their interview in August, Rihanna spoke about her memories of her father Ronald Fenty being physically abusive to her mother and how she learnt to forgive him.
Oprah said she does not think less of the popstar for reuniting with Chris.
She said: ''I think that if she is prepared to deal with that and is prepared to help him help himself then so be it. I have no judgement whatsoever. If that's how you choose to lead your life, that's really okay.''
Chris broke up with Karrueche Tran last week to give his relationship with Rihanna another chance.
The 23-year-old singer revealed he called it a day with the model because he couldn't give up his close ''friendship'' with his former flame, who he was spotted kissing at New York nightclub Griffin on Monday night (01.10.12).
Chris said: ''I have decided to be single to focus on my career. I love Karrueche very much but I don't want to see her hurt over my friendship with Rihanna.
''I'd rather be single allowing us to both be happy in our lives.''
The 'Don't Wake Me Up' hitmaker dated Karrueche since late 2011, but constant reports of his secret rendezvous with Rihanna were a source of contention in their relationship.
Over the past five years, Shia LaBeouf has gone from promising young actor to unemployable disaster and back again.
The band performed the album in full at Eaux Claires Music & Arts Festival this summer.
The band's first and only album has been re-mixed and re-mastered.
Louis Theroux incites anger from the Church of Scientology with his latest movie.
In Deepwater Horizon, Mark Wahlberg reteams with his Lone Survivor director Peter Berg.
The live album is set for released in November.
The movie begins filming in the UK.
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