Lots of great little anecdotes in this piece: http://www.nytimes.com/2016/07/03/us/politics/obama-after-dark-the-precious-hours-alone.html
Some tidbits:
WASHINGTON — “Are you up?”
The emails arrive late, often after 1 a.m., tapped out on a secure BlackBerry from an email address known only to a few. The weary recipients know that once again, the boss has not yet gone to bed.
…
Last month it was a 12:30 a.m. email to Benjamin J. Rhodes, the deputy national security adviser, and Denis R. McDonough, the White House chief of staff, telling them he had finished reworking a speechwriter’s draft of presidential remarks for later that morning. Mr. Obama had spent three hours scrawling in longhand on a yellow legal pad an angry condemnation of Donald J. Trump’s response to the attack in Orlando, Fla., and told his aides they could pick up his rewrite at the White House usher’s office when they came in for work.
Mr. Obama calls himself a “night guy,” and as president, he has come to consider the long, solitary hours after dark as essential as his time in the Oval Office. Almost every night that he is in the White House, Mr. Obama has dinner at 6:30 with his wife and daughters and then withdraws to the Treaty Room, his private office down the hall from his bedroom on the second floor of the White House residence.
There, his closest aides say, he spends four or five hours largely by himself.

Some tidbits:
President George W. Bush, an early riser, was in bed by 10. President Bill Clinton was up late like Mr. Obama, but he spent the time in lengthy, freewheeling phone conversations with friends and political allies, forcing aides to scan the White House phone logs in the mornings to keep track of whom the president might have called the night before.
“A lot of times, for some of our presidential leaders, the energy they need comes from contact with other people,” said the historian Doris Kearns Goodwin, who has had dinner with Mr. Obama several times in the past seven and a half years. “He seems to be somebody who is at home with himself.”
To stay awake, the president does not turn to caffeine. He rarely drinks coffee or tea, and more often has a bottle of water next to him than a soda. His friends say his only snack at night is seven lightly salted almonds.
“Michelle and I would always joke: Not six. Not eight,” Mr. Kass said. “Always seven almonds.”
Michelle Obama occasionally pops in, but she goes to bed before the president, who is up so late he barely gets five hours of sleep a night. For Mr. Obama, the time alone has become more important.
In 2009, Jon Favreau, Mr. Keenan’s predecessor, gave the president a draft of his Nobel Prize acceptance speech the night before they were scheduled to leave for the ceremony in Oslo. Mr. Obama stayed up until 4 a.m. revising the speech, and handed Mr. Favreau 11 handwritten pages later that morning.
The president also uses the time to catch up on the news, skimming The New York Times, The Washington Post and The Wall Street Journal on his iPad or watching cable. Mr. Love recalls getting an email after 1 a.m. after Mr. Obama saw a television report about students whose “bucket list” included meeting the president. Why had he not met them, the president asked Mr. Love.
Mr. Obama and his wife are also fans of cable dramas like “Boardwalk Empire,” “Game of Thrones” and “Breaking Bad.” On Friday nights — movie night at the White House — Mr. Obama and his family are often in the Family Theater, a 40-seat screening room on the first floor of the East Wing, watching first-run films they have chosen and had delivered from the Motion Picture Association of America.