Barbara Walters' Biggest Bloopers

Barbara Walters is celebrating three decades of primetime interviews with a lighthearted, poignant, and often hysterical two-part program, "The Barbara Walters Special: 30 Mistakes in 30 Years."

Walters shares her interviews with world leaders, athletes, musicians and Hollywood icons, chronicling her mistakes … and theirs.

The special includes classic candid moments with stars including Al Pacino, Will Ferrell, Eddie Murphy, Lucille Ball, Patrick Dempsey, Jamie Foxx, George Clooney, Teri Hatcher, Brad Pitt, Halle Berry, Jerry Seinfeld, President Ronald Reagan, and countless others.

Here, Walters highlights her lowlights from the past 30 years:

Mistake # 30: Never ask anyone what kind of tree they want to be.

It was 25 years ago when Walters asked Katharine Hepburn that question. It's a moment that has dogged her throughout her career.

#29: Never gush over a future president.

A sappy good night to then-President-elect Jimmy Carter and his wife, Rosalynn, on her very first special in 1976, is a clip that still makes Walters cringe.

#28: It's one thing to ask about embarrassing pictures, it's another thing to embarrass a guest.

Walters asks numerous women why they posed nude for a magazine, but with Suzanne Somers she takes the questions a little too far.

#27: Never ask people how much they're worth, it's rude. … Unless it's Donald Trump.

Forget not talking about money: Walters has asked celebrity after celebrity about their financial status -- even 11-year-old Dakota Fanning.

Nothing is off-limits when it comes to "The Barbara Walters Special," and through the years, Walters has asked her interviewees about everything from their bank accounts, to their looks … to losing their virginity.

#26: Enough already with the virginity talk!

Walters discusses losing one's virginity with leading men Patrick Dempsey, Don Johnson, Ricky Martin and Liam Neeson.

#25: If you're beautiful, stop saying you're not. It's irritating to the rest of us.

This mistake was made by some leading ladies, when Walters asked Hollywood beauties like icon Lauren Bacall and Halle Berry how they really feel about their looks.

# 24: If you don't think someone is sexy or attractive, don't say it.

In humorous conversations with Bette Midler and Tom Hanks, Walters is a little too honest about her opinion of their looks.

In 30 years of specials, Walters has sat down with countless couples, and some of them might regret what they said. Walters herself has one big regret when it comes to her own dating life.

# 23: Never turn down dinner with Clint Eastwood.

Walters shares how she let a date with Clint Eastwood slip through her fingers.

#22: Sitting down with your mate can lead to trouble.

In another mistake attributed to her guests, celebrity couples such as Michael Douglas and Catherine Zeta-Jones sometimes say things that surprise even their better half.

#21: Never talk about the ex-husband in front of the current husband.

In an interview with Lucille Ball and new husband Gary Morton, Ball poignantly recalls her failed marriage to Desi Arnaz. She and Carol Matthau have a more humorous exchange on the subject of her ex-husband, William Saroyan, in front of actor Walter.

Walters often shoots her interviews weeks before they air, so she continually asks people not to make any life changes before the show airs. Still, some people simply ignore her advice and live life on their own terms.

#20: You can't trust David Duchovny.

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