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.
Wow...you'd think he'd give at least one to someone who isn't one of his liberal Democratic supporters, just to maintain the illusion that the award still means something.
Is there anything this man can't cheapen into a meaningless political payoff?
He gave an award to country music star Loretta Lynn. This is such a sad attempt at political bribery it's pathetic.
I think the President should have had one more left after the 16 and should have just placed it around his neck for freeing so many people from their existing health plan!!
Sounds more like a celebrity award than a civilian award. How about spending your time trying to reduce the national debt or doing something to help the real civilians?
Typo in the last sentence: JFK's 'gave' site
I can hardly wait until the next Democrat president gives the Medal of Freedom to Obama for our new found freedom of forced healthcare insurance purchase. Probably sometime around 2075 or maybe even 2125 given the scale of the Obmacare disaster.
Dog and Poney show
Ah, giving out that medal like so much cheap wine
..... and people used to laugh at the Russians for almost randomly giving out "Hero of the Soviet Union' medals.
Clinton? Former US President and Commander-in-Chief of our armed forces. If I acted as Clinton did during my time in the Army, I would have been dishonorably discharged. That medal looks great on him.
"Medal of Freedom", right, seems to me they are giving them out like candy and stretching the idea behind it. Seems like just another political stunt. This country is a shadow reflection of what it once was, things seemed like they were getting better but it is all just a smoke screen. Nothing has changed, only on the surface, the PRBS surface.
Anyone else have a load of bile stuck in the back of the throat? I think I will skip lunch now...
Just another fraud contest from President Charlatan.
what a country... where you can be impeached and disbarred, then, receive the nations highest honors!
Not one of them is deserving of this medal especially Oprah.
Great work Pres. Obama and Clinton. Pres. Clinton vs. GW Bush is like comparing Earth to Mars. GW Bush didn't know his right from his left..
Sad group. Only Sally deserves it.
Way to celebrate the wrong spirit of JFK by bizzaro Obama thinking "Ask not what you can do for yourself, but what the government can hand out to you" .
Hmm, something seems a little odd about the recipients.
that looks so bogus...please every one dont need a trophy
I think President Kennedy might be a little disappointed to see who has received this award in the last 30 or so years.
An award from Obama is absolutely nothing to be proud of. Old Bill Clinton looks like he may have been turned to drinking a little.
Even the medals are not spared ! they are given to close buddies !