The former Democratic president and Republican house speaker from Ohio often clashed on policy — famously so when the 2011 "grand bargain" budget deal fell apart — but still maintained a respectful working relationship while Boehner was speaker.
The two would famously discuss strategy and hash out disagreements in the Rose Garden outside the White House, during which Boehner would smoke cigarettes and Obama, a former smoker, would chew nicotine gum.
Boehner even recalled having to "sneak in" into the White House to meet with Obama to avoid the press from "going crazy."
"We were having a nice conversation and finally the president says, 'Boehner, man, I'm going to miss you," Boehner said of Obama's phone call to him after he retired as Speaker of the House in 2015.
Boehner even made a cameo in a comedic video Obama showed at the 2016 White House Correspondents Dinner during which they joked around and watched "Toy Story."
"I understand him, he understands me, and while we had big disagreements, we were able to get an awful lot of things done, somehow. Don't ask me how," he added.
Sources: Cleveland.com, Business Insider, Washington Post, Vox