Oprah and Dr. Phil (1998)

In 1995, Oprah hired former psychologist Phil McGraw's consulting firm to help her navigate the Texas beef trial. After her victory, Oprah invited the straight-talking "Dr. Phil" on her show in 1998, effectively launching the mustachioed self-help mogul's television career. He soon became a weekly guest, appearing Tuesdays as a "relationship and life strategy expert" to offer advice on parenting, weight loss, financial planning and romance. In 2002, Dr. Phil graduated to his own show, produced by Winfrey's Harpo Studios.<br>
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( John Shearer / Getty Images / August 30, 2009 )

In 1995, Oprah hired former psychologist Phil McGraw's consulting firm to help her navigate the Texas beef trial. After her victory, Oprah invited the straight-talking "Dr. Phil" on her show in 1998, effectively launching the mustachioed self-help mogul's television career. He soon became a weekly guest, appearing Tuesdays as a "relationship and life strategy expert" to offer advice on parenting, weight loss, financial planning and romance. In 2002, Dr. Phil graduated to his own show, produced by Winfrey's Harpo Studios.

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