President Obama's best sports jokes during his presidency

0:59 | Extra Mustard
President Obama welcomed Cubs to White House with jokes
Monday January 16th, 2017

President Obama welcomed his final sports team to the White House on Monday as the Cubs' celebrated their first World Series championship in 108 years.

Over the past eight years, Obama has established himself as arguably the best comedian among his 43 predecessors. President Clinton and President Regan had a good grasp on comedy but Obama's delivery, (sometimes) self-deprecating humor and wit has been a treat to watch at the White House Correspondents’ Dinners and team White House visits.

There's been no shortage of Chicago jokes, as Obama is always the first to remind us that he is a die-hard White Sox and Bulls fan. It works sometimes and falls flat on other occasions.

Let's take a moment to laugh and cringe at some of the Comedian-In-Chief's finest moments over the years:

22. While in Boston in 2012, Obama made a little quip about Kevin Youkilis leaving the Red Sox for the White Sox.

“Finally Boston, I just want to say: Thank you for Youkilis.”

The crowd booed, although the White House later said that the crowd was actually chanting "Youk!" as they did before his at-bats at Fenway. The damage control only went so far as Youkilis hit .236 in his only season in Chicago.​

21. A very 2014 joke.

"Hunter Pence eats pizza with a fork."​

20. If it wasn't for Peyton Manning, no one may have laughed at this “Omaha!” joke from the Denver Broncos' visit in 2016.

He showed some love to Manning shortly after the joke.

"Then there's this guy from the commercials. No matter what you need -- insurance, a pizza, a Buick -- you basically can stack your whole household with stuff this guy is selling."

19. We learned Obama shares a lot in common with Luke Walton.

“Unfortunately, the NBA won’t let Luke count those wins as his own – which, man, that doesn’t seem fair,” You defied the cynics. You accomplished big things. You racked up a great record. And you don’t get enough credit. I can’t imagine how that feels.”

And he has a good impression of Stephen Curry.

#https://vine.co/v/iJTxt9TwAxj

18. Roll tide.

"This is the fourth time I have hosted Alabama here at the White House...in fact you could call me O-‘Bama."

17. Obama greeted the 1972 Miami Dolphins to the White House 40 years after the team made history by going 17–0. The team did not visit the White House in their playing days—the athlete visit to the White House was not an established tradition and President Richard Nixon was entrenched in the Watergate scandal. Obama took the opportunity to make a crack about his age.

“I know that some people may be asking why we’re doing this after all these years. And my answer is simple: I wanted to be the young guy up here for once.”

16. We've seen the David Beckham Calvin Klein ads and so has Obama.

"In fact, it is a rare man who can be that tough on the field and also have his own line of underwear. David Beckham is that man."

15.Obama welcomed Team USA after the Rio Olympics and gave credit to many of the amazing performances from Simone Biles, Katie Ledecky and more.

“I was nervous she was going to ask me to hold all her medals while I was speaking,” Obama said of Ledecky. (Just four years earlier, he said, “Katie Ledecky may have been swimming in London, but she still had to finish summer reading assignments.”)

With more than 500 athletes in the room, he knew when to wrap it up.

"If I keep on going longer, I'm gonna get, like, Phelps face from you guys."

14. The Chicago Blackhawks made three trips to the White House under Obama. By the time they rolled around in 2015, Obama credited himself for some of the good luck and asked for a little help in return.

"It is also, by the way, a tribute to the head of scouting, who just told me that he could help me pick my Supreme Court justice. He volunteered. He said 'I know what I'm doing.'”

13. In his final event at the White House, Obama also tried to tap into Theo Epstein's expertise in ending droughts.

"I've talked to him about being DNC chair."

Obama also noted that Jon Lester and David Ross saying "I love you, man" to each other was an "Obama-Biden" moment.

12. Hockey Twitter lost its mind over this joke.

“It is wonderful to be here, and welcome to the White House. We are here to celebrate an extraordinary achievement…Phil Kessel is a Stanley Cup champion.”

11. When it comes to singing and dancing, Obama has not sung as much as we have hoped. We can still say that he might be a better singer than Dirk Nowitzki.

"Clearly Dirk is a tough guy, although the most painful thing may have been his rendition of 'We Are the Champions' during the victory celebrations."

10. It takes a lot of courage to make a joke about Ray Lewis to his face. Obama did it when the Ravens visited in 2013.

"Ray retired on top, coming back from a triceps injury, which I believe was caused by that dance he does. But no, I'm not doing that dance. It caused him to miss most of the regular season."​

9. Being the President does not allow you to recycle jokes unnoticed. There's this short one on Gronk from the Patriots' visit.

"I told him to keep his shirt on. He asked me what would happen if he took it off. I said, 'Secret Service probably wouldn't like it.' He said, 'What could they do to me.'”

Which he later adapted for J.R. Smith's recent visit with the Cavaliers.

“I also, before I go any further, want to give a special thanks to J.R. Smith’s shirt for showing up. I wasn’t sure if it was going to make an appearance today. I’m glad it came. You’re a very nice shirt.”

8. If Vin Scully announced the Presidential Medal of Freedom ceremony, we would not have this little gem.

“When he heard about this honor, Vin asked with characteristic humility, ‘Are you sure? I’m just an old baseball announcer.’ And we had to inform him that, to Americans of all ages, you are an old friend. In fact, I thought about him doing all these citations, which would have been very cool, but I thought we shouldn’t make him sing for his supper like that.”

7. In his eight years as president, there was no shortage of Chicago jokes. He got another one in at the Warriors' expense.

“I should add, that by knocking off the Warriors, they cemented the 1996 Bulls as the greatest team of all time. So your president thanks you for that.”

6. Grayson Allen is actually tripping people for the future Trump shout-out. Obama shared the stage with Allen and the 2015 Duke basketball team and little did he know that one of the most despised recent Duke players was on stage with him.

"When I flip on ESPN and see a documentary about how people still 'hate' Christian Laettner, a guy who played for Duke 23 years ago, I realize, well, maybe I don't have it so bad...or I think this is going to be a long 23 years."

5. Charles Barkley lost his mind at Kris Jenkins' game-winning shot at the 2016 NCAA tournament and Obama took advantage.

"That was a good shot. It was like a Christian Laettner shot. It was like a Jimmy V running up and down the court shot. Charles Barkley apparently jumped out of his seat, which he doesn’t do very often these days."

4. The Cubs visit the White House, which is something that had never been done before.

“They said this day would never come...”

3. This is why Belichick voted for Trump.

“I'm part grateful that coach decided to dress up today. Formal hoodies are allowed.”

2. At this point Michael Jordan has to know that a whole generation might know him as a meme and not the greatest basketball player of all-time. Obama added a little bit of salt to the wound before presenting him with the Presidential Medal of Freedom.

"MJ is more than just a logo. He's more than just an internet meme"

1. A Deflategate joke while on stage with the Patriots. Priceless.

"I usually tell a lot of jokes at these events but with the Patriots in town, I was afraid 11 out of 12 of them would fall flat."

A new era of comedy will soon begin as Donald Trump will welcome the Clemson Tigers to the White House to celebrate their college football national title in the coming months.

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