Chicago Oprah Watch

20 worst Oprah moments

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Mallory Hoke

ChicagoNow Life & Style Community Manager

With the recent announcement that Oprah will be retiring, we decided to celebrate by highlighting O's 20 worst moments. Feel free to add in any that we missed, and  let's party like it's 2011 already. Click through the photos below for Oprah's most awful: 

Gallery sneak peek (20 images):

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Oprah show ending in 2011

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Jimmy Greenfield

ChicagoNow Community Manager

The rumors apparently are true. Oprah Winfrey will be ending her talk show in 2011, according to the Associated Press.


Gallery sneak peek (29 images):

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Sarah Palin To Appear on The Oprah Winfrey Show

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Breaking Tweets Chicago: Sarah Palin to appear on Oprah Nov. 16

Taylor Swift Tells Oprah She Accepts Kayne's Apology

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

On today's episode of The Oprah Winfrey Show, Taylor Swift said she has accepted Kanye West's apology for interrupting her acceptance speech at the MTV Video Music Awards.

I'm puzzled as to why people think this is news because Swift already said--nearly four weeks ago, mind you--that she accepted his apology.  Perhaps apologies don't count unless you publicly accept them on Oprah?

Regardless, Swift elaborated on why she was so willing to forgive:

"I feel like being raised by two parents who basically brought me up with the idea that the world didn't owe me anything really helped...My whole life, I just loved music and I'd see these people on big stages, and I didn't think I could actually do that."

Statements like this only make me wonder how much longer Taylor will remain this innocent and pure--and how long it'll be before she's back on Oprah's couch talking about her drug addiction and wild sex life.  Doesn't everyone end up pulling a Britney nowadays, anyway?  (Hello, Lindsay Lohan!)

Columbine killer's mother opens up in Oprah Magazine

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

According to the Chicago Tribune, the November issue of O, The Oprah Magazine, will feature an essay by Susan Klebold, whose son Dylan was responsible for the Columbine Massacre in 1999.

Although Klebold testified in a lawsuit related to the tragedy, this is the first time she's speaking publicly.  And, according to a family spokesman, she won't be again.

Dylan and classmate Eric Harris killed 12 students and a teacher, and injured countless others, when they opened fire at Columbine High School in Denver.


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Derrion Albert's Mother, Mayor Daley on The Gayle King Show

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Gayle King, Oprah's long-time friend and collaborator, dedicated the Friday edition of her Sirius XM radio show (which airs on the "Oprah Radio" station) to the tragic death of Derrion Albert and the issue of violence among the nation's youth.

King interviewed both Mayor Richard M. Daley and Derrion's mother, Anjanette Albert.

Audio and video after the jump.

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Oprah's Harpo Sued

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Another day, another bizarre Oprah lawsuit...

Head over to Chicago Bar-Tender for all the details.

Related: Oprah's Court Battles--A Timeline

Mike Tyson To Appear on Oprah Winfrey Show

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

When I first read the press release announcing Mike Tyson's upcoming appearance on next Monday's edition of The Oprah Winfrey Show, I was perplexed.

Mike Tyson?  Really?

He's not an A-list celebrity.  There's no newsworthy controversy surrounding him right now.

And then I remembered.  Less than five months ago, Tyson's 4-year-old daughter died after a strange accident involving a treadmill machine.
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Chicago 2016 Olympics: What Oprah Wants...

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

You want Obama to win the presidency?  Sure thing.  Close down Michigan Avenue?  Not a problem.  The Olympics in Chicago?  Hold up a second.

After traveling to Copenhagen to plead Chicago's case before the International Olympic Committee, Queen O must be mighty shocked the city was eliminated this morning in the first round of voting. For the first time in recent memory, what Oprah wants isn't what Oprah gets. 
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All Hail Queen O: Oprah Show Ratings Rise Dramatically

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

All hail Queen O.  All hail Queen O.

In the words of the Chicago Tribune's Phil Rosenthal, Oprah is "back on her game."

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Oprah Going to Copenhagen with Chicago's 2016 Olympic Committee

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

In anticipation of the International Olympic Committee's decision on the location of the 2016 Olympics, on October 2 Oprah Winfrey will travel to Copenhagen with Chicago's official delegation.
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Mackenzie Phillips Reveals Incest Past on Oprah

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

PHOTO GALLERY: See the Oprah Show's past big reveals

On today's Oprah Winfrey Show, former Mamas and the Papas member Mackenzie Phillips revealed a decade-long incestuous affair with her father, John Phillips.

The internet is buzzing today with the news, which will be explained even further in Phillips' upcoming memoir High On Arrival.

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First Chicago, Now New York: It's The Oprah Winfrey Show

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Oprah's at it again.

According to The New York Times, Queen O "will broadcast live from Rumsey Playfield" in Central Park on Friday.

Sound familiar?  Sure it does.  Just replace the Black Eyed Peas with Mariah Carey, and add in a little Regis Philbin and Kelly Ripa.

But unlike Oprah's kick-off party on Michigan Avenue last week, you must reserve tickets for the taping in advance and you must be older than 18.

Just know you were first, Chicago!

Oprah Jaycee Dugard interview?

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Amy Guth

Amy Guth is digital news editor for the Tribune's books section and blog and is co-host of ChicagoNow Radio on News 720 WGN alongside Alex Quigley. Also? Author, adventuress and grade-a sass-mouth.

Breaking Tweets Chicago reports on one of today's top rumors: that Oprah may, in fact, interview Jaycee Dugard, the 29-year old woman who was recently found after being kidnapped at age 11.

Read full story and follow latest on Twitter at Breaking Tweets Chicago.

OprahDay: time-lapse of Michigan Ave.

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Amy Guth

Amy Guth is digital news editor for the Tribune's books section and blog and is co-host of ChicagoNow Radio on News 720 WGN alongside Alex Quigley. Also? Author, adventuress and grade-a sass-mouth.

Time-lapse video of Michigan Ave. leading up to Oprah event, then repeating backwards, as seen from outside the Tribune Tower.

What if Oprah was a man?

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Teresa Puente of ChicanĂ­sima says we need a Latina Oprah.  That may be true.  But can we start small first?  How about a male Oprah? (No pun intended.)
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Oprah takes Michigan: here's what you missed

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Amy Guth

Amy Guth is digital news editor for the Tribune's books section and blog and is co-host of ChicagoNow Radio on News 720 WGN alongside Alex Quigley. Also? Author, adventuress and grade-a sass-mouth.

Oprah took over Michigan Avenue on Tuesday. But this, surely, you know.

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Preparations, super-fans and transportation: Monday, preparations were underway for Oprah's 24th season kickoff on Michigan Ave., and by Tuesday morning, the final set-up was completed. Oprah's super-fans arrived early to stake out ideal spots, thought the big crowds didn't begin to pour until just before 9am. Though we braced for serious commuter mayhem due to Michigan Ave. turning from major thoroughfare to massive block party, things went relatively smoothly, if Twitter is any indication. Perhaps we have Chicagosphere's guide to navigating Oprah's street closures and Oprah's diva detour survival guide to thank?

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Love, lawsuits and Olympic speculation: Think of all Oprah has done (and worn, for better or for worse!) since her show started all those years ago. It hasn't all been rosy, take her legal battles for example, but today, we overheard people in the crowd, and online, discussing the many ways they each felt connected to Oprah over the years, much of which is discussed in Jenny Prokopy's Does this city make Oprah look fat?, L-blog's Why lesbians should care about Oprah and Jen Weigel's Oprah is spiritual, damnit! Of course, there was discussion of another kind going on, too, captured in Craig Kanalley's Is Oprah's Chicago shutdown really about the 2016 Olympics?  

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Waiting for Oprah: By midday on Michigan Avenue, the people were waiting. And waiting. And doing loudspeaker-led dances we later turned into contests. And waiting. RedEye's Ernest Wilkins brought reading material and chatted people up who were waiting patiently for Oprah while Breath, Body and Balance's Maya Henderson offered yoga poses for people stuck waiting in place all afternoon. Even at ChicagoNow, we tried different things to amuse ourselves while waiting Oprah's arrival including Oprah acrostic, pick-the-book-Oprah-would-never-endorse, six-degrees of Oprah, in addition to the aforementioned photo caption contest.  Uh, and maybe we watched video of Oprah discussing her "va-jay-jay". Perhaps.

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Oprah, the show and her guests: And then, Oprah arrived on a double-decker red bus, with Mario Lopez, during Jennifer Hudson's sound check. Oprah took to the stage on Michigan Avenue shortly after 5pm on Tuesday evening wearing a yellow top and jeans. (Overheard: "Is that Olympic yellow she's wearing?") The Black Eyed Peas started off the show, which included a crowd-embedded flash mob who broke into choreographed dance, followed by Criss Angel (whom we spotted strolling around Monday evening), Rascal Flatts, Jennifer Hudson and James Taylor. Lots of tweets and twitpics surfaced during the show, with some highlights showcased on Breaking Tweets Chicago

In the end: At evening's end, the Chicago Police reported zero arrests, not even as much as slightly rowdy behavior from any of the estimated 20,000-ish people in attendance (which is excellent news considering the finer points on the Oprah-logistics raised by Joe the Cop), and Oprah thanked her festive crowd, the city of Chicago and Mayor Daley before leaving the stage.

Oprah's 24th season opener will air Thursday, September 10th.

Did You Miss Oprah Day on Michigan Avenue?

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

No worries! Today's taping will air Thursday, Sept. 10, as the official premiere of The Oprah Winfrey Show's 24th season.

But if you can't wait to see what went down, this is the best recap we've seen yet.

Oprah and Criss Angel: WTF Was That?!

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Color me confused.  Something having to do with a locked box, a beach ball and some mind trick? 

Apparently
, sometime before today (or so we're supposed to believe), Angel made predictions about the show and what Oprah would give away.

And gosh golly gee, he was right. Color me stupid.  'Cause I just don't get it.

Say it with me now: This. Was. A. Set-up.  Right?  RIGHT?!


The Black Eyed Peas Just Performed With Oprah on Michigan Avenue!

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

At least, that's what it looked like from our window.  Don't fret.  This performance was likely better or, you know, exactly the same:


Oprah Day on Michigan Avenue: It's Showtime!

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

We're minutes away from the official taping of "The Oprah Winfrey Show" right outside our offices on Michigan Avenue.

Are you there?  Send tweets and TwitPics to @ChicagoNow.

Stuck at home?  Or worse, work?  Comment below with your laments.

Worried About Oprah Day? Don't Ask The Chicago Police

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

ChicagoNow Social Media Intern Mallory Hoke did a little sleuthing earlier...and didn't get very far. Mallory spoke with the Chicago police officers stationed in the lobby of Tribune Tower, seeking answers to some of the most important questions of the day:

-what happens if there's thunder and lightning?

-what happens if there's a torrential downpour?

-what happens if a fan gets too rowdy?

Their answer? "We can't answer."  No, actually, you can. You just won't.

John Cop and Jane Officer told Mallory that there are plans in place, but they can't divulge them.  So much for public awareness!  Take comfort knowing the CPD will protect you...you just won't know how.

Oprah's Most Popular Guests

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

...aren't in Chicago.  We think.

But then again, most popular isn't necessarily equal to most frequent, which is what we're really talking about.

These 5 celebs have been on The Oprah Winfrey Show more than any other guests:

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Leave Oprah Alone!

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Britney had Chris Crocker.  Oprah has this guy...

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Oprah and That Other O (Obama!)

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Remember him?  He's just, oh, the PRESIDENT OF THE UNITED STATES! 

We know who's been here longer (Oprah).  We know who better fix the economy or else (Obama).  We know who the city shuts down for (both, apparently).

But: who is better known overseas?  Who is truly the global superstar?
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Oprah "Fake Caption" Contest

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Jimmy Greenfield

ChicagoNow Community Manager

What are these people waiting in line for Oprah Winfrey doing? Write in your caption in the comment field below.

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Photo by Chicago Tribune


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Oprah's court battles, a timeline

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Fernando Diaz

ChicagoNow community manager for news and opinion

Oprah's run-ins with the court system have been tons more interesting than her shows (but I'm a guy, so what would I really know.) She's tussled with Texas cattle ranchers, photographers and spurned fans and even a Canadian tabloid that attempted to spread some vicious rumors about her b-friend Stedman Graham. And somehow, the Queen of Talk has emerged unscathed. From $1 trillion to a couple hundred thousand, there is a colorful cast of characters in Oprah's dances with the justice system.

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Chicago Blogosphere Tackles Oprah Day

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Ohhhhh OPRAH!: OPRAH Shutting Down the Street Music Video

Oprah Kickoff Party Prep

Photos: Oprah on Michigan Avenue

From the Scene: Oprah's Block Party

Tourists Excited for Oprah's Michigan Ave. Show

Oprah Fans Describe Scene of 24th Anniversary Party as "Bum-Rush," "Mini Woodstock"

Oprah and Twitter: Epic Fail?

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Much hulabaloo was made when Lady O joined the microblogging site in April.  But with tweets few and far between, Oprah hardly deserves a spot in the Twitterati.  Afterall, she may have more than 2.1 million followers (hear that, Ashton?) but she's only following 15 (all celebrities, mind you).  And, in the words of our own Amy Guth, she got "skuh-ooled" by Shaquille O'Neal in Twitter ettitquette. Interaction?  Forget it.
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Track Oprah Day With Live Tweets!

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Shari Weiss

ChicagoNow's social media intern; owner and operator of TeenDramaWhore.com; editor of BreakingTweets.com/entertainment

Stay atop of the Oprah Day madness (or is it goodness?) with this feed of live-tweets. The feed will update every 15 seconds. And be sure to add your two cents in the comments!

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