From a few accidentally-on-purpose innuendos to slips of the tongue and sticking it to difficult guests, Oprah Winfrey knew how to make good TV during her 25-year run hosting The Oprah Winfrey Show, which left the air in 2011.

However, on Monday's episode of Harry, the roles were reversed when host Harry Connick Jr. had Miss Winfrey in the hot seat to promote her latest book, The Wisdom of Sundays: Life-Changing Insights from Super Soul Conversations.

When the crooner-turned-talk-show host asked the media mogul who her "worst" guest ever was, the billionaire producer revealed that a  lawyer who couldn't stop name dropping his book topped her naughty list.

That got us thinking about her many jaw-dropping moments over the years, which there were plenty of, as well as her plethora of awkward encounters with guests.

Check out the top five most awkward interviews over the years...

5. The Time Barbra Streisand Spray Painted Her Mic to Match Her Sweater and Her Dog...

Few of Oprah's interviews have been made fun of as much as the time Babs hit the show with an all-ivory ensemble, complete with ivory lapdog. The now-infamous interaction was later parodied by both Kathy Griffin and Mad TV.

In fall 2003, the Funny Girl star stopped by Harpo Studios to perform a single diddy. After the song, Miss O couldn't help but point out that the big-voiced songstress had spray painted (or rather instructed an employee to spray paint) the usually black mic to match her carefully orchestrated outfit.

When Lady O called her out, Barbra said, "I like simplicity and monochromatic frames so I thought just look that if the mic melts in my sweater...in other words, it just makes the focus on the song."

Controlling much? You be the judge. 

4. The Time Mackenzie Phillips Said She Had a Sexual Relationship With Her Father, Mamas and the Papas' singer John Phillips...

There wasn't a lot about this interview that wasn't uncomfortable to watch. No need to elaborate.

3. The Time When Oprah Didn't Pull Any Punches With Jay Leno...

After Leno was ousted from The Tonight Show in favor of Conan O'Brien, who then got canned in order to bring back the car-loving comic, the formerly beloved funnyman was on the outs with the public and sat down with the mogul.

Oprah grilled her friend with a series of tough questions: "Were you embarrassed about how all of this transpired?" "Did you ever ask yourself, 'Am I being selfish?'" "Do you think celebrities will still come on your show?" and "Do you think you can be No. 1 again?"

Sometimes not even being pals with the host can get you out of the line of fire.

Tom Cruise, The Oprah Winfrey Show

Harpo Productions / CBS Television Distribution

2. That Time Tom Cruise Jumped on a Couch Because He Loved Katie Holmes So Much...

No episode has been made fun of more than the time the Mission: Impossible star proclaimed his love for his new girlfriend atop a plush piece of furniture. No couch has ever been the same and no one looked more shocked by the bold move than Oprah. It was a lot. Like a lot, a lot.

James Frey, Oprah Winfrey

Harpo

1. That Time that Oprah Reminded James Frey You Don't Mess With Oprah...

Oprah left us all in a million little pieces when she stuck it to the author of A Million Little Pieces after it was was revealed that Frey had fictionalized key parts of the supposed memoir, which the talk show host had proudly championed on her show and in her Book Club.

In the interview, Oprah said she felt "betrayed" and then basically let the fallen scribe have it for an hour.

She's later said that she let her anger towards him get the best of her and has since apologized to the writer.

What do you think the most awkward Oprah interview was? Sound off in the comments!

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