The BEST episodes of The Oprah Winfrey Show season 23

Every episode of The Oprah Winfrey Show season 23, ranked from best to worst by thousands of votes from fans of the show. The best episodes of The Oprah Winfrey Show season 23!

The Oprah Winfrey Show has featured many celebrities over the years, but that's only one side of it. There's also Oprah's eternal quest to better herself, and to help viewers do the same.

Last Updated: 9/6/2024Network: AudienceStatus: Ended
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#1 - Losing Weight in the Public Eye with Star Jones, Valerie Bertinelli and Marie Osmond

Season 23 - Episode 104 - Aired 4/1/2009

For the first time, Oprah talks to Star Jones—the 160-pound weight loss, The View, the truth. Plus, Valerie Bertinelli's new bikini body and Marie Osmond!

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#2 - Released from Prison: A Mom of 3 Goes Home

Season 23 - Episode 116 - Aired 4/20/2009

Lisa Ling and our cameras ride along on a major pornography bust—as it goes down. Then, after three years in prison, follow a mom's journey home.

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#3 - Oprah Twitters with Ashton Kutcher

Season 23 - Episode 115 - Aired 4/17/2009

Have you heard about Twitter? Millions are hooked on it. Oprah's getting ready to send her very first tweet! And, why Ashton Kutcher's being crowned the king of Twitter.

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#4 - They Say They're Ready to Have Sex

Season 23 - Episode 114 - Aired 4/16/2009

At 14 years old, they say they're ready to have sex. Dr. Laura Berman is taking charge. Ready or not…the questions you need to sit down and ask your teen.

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#5 - Held Captive as a Sex Slave

Season 23 - Episode 113 - Aired 4/15/2009

Seduced online…even one mom's strict rules couldn't protect her daughter. Plus, a plea from America's Most Wanted's John Walsh. Get the facts you need to know.

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#6 - Stars of Country Music

Season 23 - Episode 112 - Aired 4/14/2009

The biggest names in country music are hitting our stage! Plus, you know him as Hootie…now Darius Rucker is making history!

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#7 - Unconventional, Unforgettable Dads

Season 23 - Episode 111 - Aired 4/13/2009

Meet a dad who's raising nine kids all on his own! Then, why thousands of moms are helping a father they've never met. Plus, a soldier dad's unforgettable words.

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#8 - James Taylor

Season 23 - Episode 110 - Aired 4/10/2009

He's sold over 40 million albums. Five-time Grammy winner James Taylor joins us for an amazing performance!

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#9 - Recession-proof your marriage

Season 23 - Episode 108 - Aired 4/8/2009

Get the step-by-step action plan to recession-proof your marriage and your family. M. Gary Neuman has crucial advice for every couple in crisis over money.

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#10 - How To Talk to Your Kids About Sex

Season 23 - Episode 109 - Aired 4/9/2009

One mom is having "the talk" with her daughter on TV to help you start your own conversation. Plus, Dr. Laura Berman with the exact words to say to your kids.

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#11 - Secret Lives of Moms

Season 23 - Episode 107 - Aired 4/6/2009

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#12 - Women Reveal What They Really Want

Season 23 - Episode 106 - Aired 4/3/2009

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#13 - Recession Rescue with Suze Orman

Season 23 - Episode 105 - Aired 4/2/2009

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#14 - Oprah's Most Memorable Guests

Season 23 - Episode 117 - Aired 4/21/2009

Look back on the interviews we'll never forget. Susan Smith's ex-husband, the Boylan family and more. Plus, an update from Ted Haggard and his wife.

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#15 - Dr. Oz and Michael J. Fox

Season 23 - Episode 103 - Aired 3/31/2009

He went through great lengths to do this interview…Michael J. Fox on his family, his 20-year marriage and his primetime return. Plus, the miracle he's waited for.

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#16 - Exclusive: Oprah Goes Inside the Yearning for Zion Polygamist Ranch

Season 23 - Episode 102 - Aired 3/30/2009

A year after the raid, Oprah goes inside the polygamist ranch. Isolated from the world…see how they live. Unprecedented access that no one's ever been granted.

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#17 - Oprah Fridays Live with Justin Timberlake

Season 23 - Episode 101 - Aired 3/27/2009

Six Grammys and millions of fans…we've got Justin Timberlake for one whole hour!

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#18 - The 900-Pound Mom

Season 23 - Episode 100 - Aired 3/26/2009

At 914 pounds, she was one of the heaviest women in the world. Then, a high school senior who weighed 800 pounds. Plus, reality star Ruby takes us inside obesity rehab.

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#19 - Women Leaving Men for Other Women

Season 23 - Episode 99 - Aired 3/25/2009

They had husbands, boyfriends…then, they fell in love with women. Plus, why women are falling hard for Work Out's Jackie Warner.

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#20 - Best-Selling Love Expert Steve Harvey and 300 Women

Season 23 - Episode 97 - Aired 3/23/2009

Steve Harvey's book is flying off the shelves, and we've got him unleashed! Want to know what men really think? Steve's answering all your burning love questions!

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#21 - Oprah Fridays Live with Kelly Clarkson

Season 23 - Episode 96 - Aired 3/20/2009

Jenny McCarthy joins the panel! Then, she's the very first American Idol. Now, chart-topper Kelly Clarkson sings her greatest hits and her number one single!

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#22 - Dr. Oz: Extreme Life Extension

Season 23 - Episode 98 - Aired 3/24/2009

Dr. Oz says the future of life extension is here! Burn up to 700 calories without exercise. Plus, the radical diet that could keep you living to 100!

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#23 - Dr. Oz: After the Diagnosis with Montel Williams

Season 23 - Episode 93 - Aired 3/17/2009

For 10 years, Montel Williams has been in the fight of his life. After a devastating diagnosis…what do you do next? Dr. Oz reports.

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#24 - Oprah's Clean Up Your Messy House Tour: Atlanta

Season 23 - Episode 94 - Aired 3/18/2009

Peter Walsh and the clutter have simple solutions to declutter your home. Plus, get 25% off at The Container Store and a Friends & Family discount coupon from Volkswagen!

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#25 - Oprah Talks to Men Who've Beaten Women

Season 23 - Episode 95 - Aired 3/19/2009

Why do men hit women? Oprah talks to the men who admit they've been abusers. Then, actress Robin Givens weighs in.