Updated 11/20/2013 at 12:19 a.m. ET
Washington (CNN) – President Barack Obama awarded the Presidential Medal of Freedom – the nation's highest civilian honor - to 16 people, from former President Bill Clinton and iconic talk show host Oprah Winfrey to the late astronaut Sally Ride, in ceremonies Wednesday.
"This is one of my favorite events every year," said the President. "This year it's just a little more special, because this marks the 50th anniversary of President Kennedy establishing this award."
Obama noted that members of the Kennedy clan were in attendance: Robert Kennedy's widow, Ethel Kennedy, and JFK grandson and son of U.S. ambassador Caroline Kennedy, Jack Schlossberg.
Obama also took the chance during the ceremony for some self-deprecating humor when referencing one of the honorees. "All of us have moments when we look back and wonder, what the heck was I thinking? I have that quite a bit," Obama said. "Psychologist Daniel Kahneman has made that simple question his life's work."
President Clinton is receiving the award for his public service in the White House and for founding, "the Clinton Foundation to improve global health, strengthen economies, promote health and wellness, and protect the environment," according to the White House.
Seven things you didn't know about two Medal of Freedom winners
Obama said that after Clinton left office, "he was just getting started, he doesn't stop."
The President added that "I'm grateful Bill as well for the advice and counsel that you've offered me on and off the golf course. And most importantly for your life-saving work around the world."
As for Winfrey, the White House said, "Winfrey is one of the world's most successful broadcast journalists ... best known for creating The Oprah Winfrey Show, " And that she, "has long been active in philanthropic causes and expanding opportunities for young women."
"Her message was always 'you can.'" Obama said. "Michelle and I count ourselves among her many devoted fans and friends."
CNN reached out to both President Clinton and Winfrey for their thoughts on receiving the award, but there was no immediate response.
In a statement,, Obama said the medal "goes to men and women who have dedicated their own lives to enriching ours."
During a press briefing last month, White House Press Secretary Jay Carney added that the award is, "presented to individuals who have made especially meritorious contributions to the security or national interests of the United States, to world peace, or to cultural or other significant public or private endeavors."
The President will headline a dinner at the American History Museum Wednesday night, that will honor all of this year's recipients and include a jazz performance by Arturo Sandoval – one of this year's honorees.
Other recipients this year include:
-Former Chicago Cubs legend Ernie Banks for being, as the White House puts it, "one of the greatest baseball players of all time. During his 19 seasons with the Chicago Cubs, he played in 11 All-Star Games, hit over 500 home runs, and became the first National League player to win Most Valuable Player honors in back-to-back years." In August, the Cubs paid tribute to Banks for receiving the Presidential Medal with a pre-game tribute at Wrigley Field in Chicago. Banks told fans, "You made it possible for me to receive this great honor." The 82-year-old added, "I didn't play in the World Series … but this to me takes the place of all the days I've spent out here that didn't make it."
-Ben Bradlee, former executive editor at the Washington Post, who oversaw coverage of the Watergate break-in.
-Sally Ride, the first American female astronaut to travel to space. Ride died last year.
-Former Sen. Daniel Inouye of Hawaii, who died last year, honored posthumously for his lifelong public service. He was the first Japanese American to serve in Congress, and represented Hawaii from the day the island state joined the Union.
-Country music star Loretta Lynn, for, "breaking barriers in an industry long dominated by men," according to the White House. She became one of the first successful female country artists in the 1960s.
-Women's rights activist Gloria Steinem, for her leadership "in the women's liberation movement," the White House said, and as co-founder of Ms. Magazine.
Past Medal of Freedom award winners include music legends Frank Sinatra, Duke Ellington and Ella Fitzgerald; civil rights icons Martin Luther King Jr., and Rosa Parks; and former presidents John F. Kennedy, Lyndon Johnson, Ronald Reagan, Gerald Ford, Jimmy Carter and George H.W. Bush.
"This year's honorees have been blessed with extraordinary talent, but what sets them apart is their gift for sharing that talent with the world," Obama said, adding, "It will be my honor to present them with a token of our nation's gratitude."
Carney noted that, "This year marks the 50th anniversary of the executive order signed by President John F. Kennedy establishing the Presidential Medal of Freedom. "Since that time, more than 500 exceptional individuals from all corners of society have been awarded the Presidential Medal of Freedom," Carney said.
The President is expected to mention JFK's legacy during his remarks Wednesday evening, coinciding with the 50th anniversary Friday of Kennedy's assassination in Dallas.
A source close to the Kennedy family told CNN that Kathleen Kennedy Townsend will formally represent the Kennedy family and its three generations when President Obama and former President Clinton lay a wreath at JFK's grave Wednesday.
The source said it is possible JFK's sister, former Ambassador Jean Kennedy Smith; and JFKs grandson Jack Schlossberg, the son of Caroline Kennedy, will also attend.
Another source familiar with the planning it was President Obama's idea to honor President Clinton with the Medal of Freedom and to invite the Clintons to the wreath laying at JFK's gave site at Arlington National Cemetery.
Similarly to his low-key commemoration of the Gettysburg Address, Obama plans a quiet tribute to Kennedy set for Friday.
The time has come to go beyond static honorary metals and the splacement of flowers to honor our national heros. The time has come to experience first hand the kind of connection he had within his roots that kept and still keeps his eternal flame eternal. How can we do this? Each and every American should go outdoors and weed out hate, symbolizing our collective desire to root out detaching, polarizing, politicizing forces, clogging our own connection to all Americans who have ever lived. It is time for us to weed out, compost, and ionize this hate as fuel for our own inner eternal flame.
Guess a 150th anniversary of Lincoln's Gettysburg address is not a big deal even though Obama exploited Lincoln over and over again as his influence throughout his first term in office.
Ok, so a failure is honoring a rapist. Where's your coverage today of Odummy's 37% approval rating?
Where is it? Lost in your Benghazi file?
Ok, so a failure is honoring a råpist. Where's your coverage today of Odummy's 37% approval rating?
Really? JFK.He was, without question, addicted to narcotic pain killers and frequently had amphetamines injected into him. was a serial adulterer. Bay of Pigs anyone???
Why do we continue to put forth this ridiculous propaganda that JFK was some sort of wonderful president. yes he was young, yes he shouldn't have been killed, yes we feel bad for his children....but that doesn't mean we should forget his personal reprehensible drug addicted behavior.
Wasn't this guy impeached? I hope Clinton has a nice cigar to celebrate...
More self aggrandizement from Obama to his "crew".
Obama says this year is special "because this marks the 50th anniversary of President Kennedy establishing this award." It's also the 150 year anniversary of the Gettysburg address which paved the way for you to the oval office. He won't be attending that though....
Winfrey? The same racist that last week said that old conservatives need to be dead? That same person?
Just repaying some of his Marxist cronies!
Here ya go Oprah... Thanks for saying that anyone who disagrees with me is a racist bigot.
To steal a joke from David Cross, isn't this made up award about one step up from "World's Greatest Grandpa?"
Second Top story:
Military veterans are dying needlessly because of long waits and delayed care at U.S. veterans hospitals, a CNN investigation has found.
Mr. Obama work with the real people about Freedom.
Oprah???? What Freedom did she give us? How to make Fat white housewives excited about losing and gaining weight!
Bill Clinton commits adultery inside the White House and gets impeached, and yet he receives a medal. Actually says more about Obama than it does Clinton, but it's still an embarrassment nevertheless.
This is the greatest moment in our nations history. Gawwwwwwwwwwd bless Murica!
What a joke. Obama ...go fetch Bill his coffee. He exposed you as a liar. Talk about the pot calling the kettle black.
Seriously, "If I had a hammer... I'd whack you in the morning"? You think Kennedy and Obama are the best? Best at what, besides being celebrities?
When you feel the need to start handing out medals to nervous supporters (Clintons, etc.) and honoring popular dead Presidents as your only hope to distract from your mounting failures and lies...the trip circling the toilet bowl is nearing the end.
@ Agnostic: really? You mean ACA is hitting its number targets? That millions won't be knocked out of coverage and/or pay more for healthcare? That the young and healthy will sign up in sufficient numbers to offset the old/sick? Still drinking the koolaid eh?
And meanwhile Rome is burning due to Obamacare.
JFK is rolling over in his grave.
I wasn't aware the Medal of Freedom had a category for Greatest Political Donation. Maybe Obama just made that one up so Oprah could get one.
So now we know who donated HEAVY to his re-election
The originator of the presidential debates, an immigrant by the name of Fred A.Kahn who also is a Holocaust survivor deservesrecognition. Why not?
It appears that the President had something better to do other than showing up at Gettysburg to pay respects to a man whom everyone knows he greatly admires and reveres.
The medal of freedom White House ceremonies are to be followed by paying tribute at JFK's eternal flame.
I'm sure he's really sorry to have missed your yahoo get-together up in Gettysburg.