Former president Barack Obama has only lost one election in his life. It was in 2000, and that defeat set him on the course for his eventual U.S. Senate run. Making Obama is a production of listener-supported WBEZ Chicago. Support WBEZ and the future of podcasts like this at https://wbez.org/making

In 2000, Barack Obama ran for Congress against a Chicago political legend. It became a contest about race and identity.

Former President Barack Obama won his first political seat in 1996. Hear what he had to learn, and the conflicts he faced, to get there. 

wbez.org/making

When Barack Obama first came to Chicago, a political transformation was happening in the city. Hear how that change inspired him.

Before he was the 44th President, Barack Obama worked as a community organizer on the South Side of Chicago. Hear how the city shaped his political ambitions.

Former President Barack Obama — along with friends, mentors, and rivals — tells the story of his climb from Chicago to the national stage. Subscribe now and don’t miss the first episode on February 8.

In our final bonus installment, the Making Oprah production team revisits an extended interview with daytime talk show legend Phil Donahue. His pioneering show, Donahue, aired from 1967 to 1996 and laid the groundwork for Oprah’s program. It tackled heady, controversial issues - and landed frothy exclusives with A-list celebrities. Donahue also used his studio audience and callers in ways that were both innovative and intimate. 

Join host Jenn White, producer Colin McNulty, and executive producer Joel Meyer as they listen back to one of their favorite non-Oprah interview from the dozens of interviews conducted for Making Oprah. 

For more than 10 years after the launch of the Oprah Winfrey Show, Oprah deliberately avoided having politicians on her show, particularly during election seasons. In this bonus episode of Making Oprah, host Jenn White talks to Oprah about the role politics played - and didn’t play - in the history of the Oprah Winfrey show.

If you look at any image from the Oprah Winfrey Show, you can pretty much figure out what decade it’s from by looking at Oprah’s hairstyle. 

In this short bonus episode, host Jenn White talks to Oprah’s longtime stylist Andre Walker about the high stakes of doing the hair of the most watched woman on television.

In the show’s final decade, Oprah and her team staged massive spectacles of increasing grandiosity, from the infamous car giveaway to a 21,000-person flash mob that shut down part of Chicago. 

“It had become increasingly more difficult to top what you’d done the year before,” Oprah told WBEZ’s Jenn White. “I mean, to the point where we literally sat in a room saying ‘What about outer space?’ ” 

That’s what we look at now: Oprah living her life at the top, pushing the boundaries of what could be done with the world’s most powerful talk show, and why it all had to end after 25 years.