Jessica Coleman was an all-American girl, who at age 15, stabbed her newborn son in the chest. The next day, Tom, the baby's father, disposed of the child's body in a nearby quarry. In 2006, Jessica spoke to Oprah via satellite from the Lorain County Jail in Ohio. Look back at that interview and find out what happened to Jessica after her release.

When Carson Kressley first met Dawn, a mother of two from Alberta, Canada, she was done up from the top of her hair-sprayed extensions to the tips of her hot pink heels. After helping her embrace her natural beauty, Carson revealed Dawn's new look. Did Dawn keep it up, or is she back to her old ways? Watch and see!

In 1987, Chilli Pepper, Oprah's cross-dressing Chicago pal, made her first Oprah Show appearance. Twenty-five years later, Chilli is still performing as a female impersonator at Chicago's Baton Show Lounge. Watch as Chilli invites cameras backstage and introduces her fellow performers.

Two years after Dawn, a mother of two from Canada, got an extreme makeunder on The Oprah Show, she invites cameras inside her home. Watch as her children, Troy and Geneva, reveal what they really thought of her natural look. Plus, find out how Geneva is following in her mom's footsteps.

In 1989, Oprah played matchmaker when she flew 20 bachelors from Alaska, a state known for its abundance of single men, to Chicago to find the women of their dreams. Now, John and Peter, two of the most memorable bachelors, look back at the frenzy the show caused. Plus, find out if they're still looking for love.

From a young age, Kaden, now 20, believed he was born in the wrong body. See why Kaden says appearing on The Oprah Show in 2004 to talk about being transgender helped others be true to themselves. Plus, Kaden offers advice to young people struggling with their gender identity.

The brothers of pop band Hanson, Isaac, Taylor and Zac, say they were turned down multiple times before being signed by Mercury Records in 1996. Watch as lead singer Taylor Hanson offers advice to young musicians.

After a trip to Africa in 2007, Zac, Taylor and Isaac Hanson, members of the band Hanson, began inviting fans to walk barefoot for one mile before each concert to support the fight against poverty. Since then, the Hanson brothers have walked more than 170 miles as part of their Take the Walk campaign. See why Isaac says these efforts inspire compassion.

While recording their third album in 2001, boy band Hanson documented their journey in a film called 'Strong Enough to Break.' Taylor Hanson, 29, says the documentary was the start of the band's second chapter. Watch as they describe how the film was a turning point in their lives.

In 2004, Angelina supported her child, Kaden, a transgender 11-year-old, when he appeared on The Oprah Show. See why Angelina says she made the tough decision to talk about Kaden's journey on national television in an effort to save his life.