Then Secretary of State-designate Hillary Clinton, center, with her press secretary, Philippe Reines, left, in 2009. Chip Somodevilla/Getty Emails from former Secretary of State Hillary Clinton's personal email account that were released by the State Department on Friday contain several interesting glimpses of her team's interactions with the media.

In two cases, the messages show her top staffers seemingly mocking reporters, dubbing one a "pain in the ass" and accusing another of engaging in behavior that's not normal "among any type of mammal."

Clinton has long been characterized as frustrated with the media, which relentlessly covered scandals during the administration of her husband, former President Bill Clinton. Her relationship with the press has been one of the early issues in Clinton's presidential campaign as she was criticized for spending her first few weeks on the trail without taking questions from reporters.

In one instance, on September 26, 2012, Clinton forwarded her then deputy chief of staff, Jake Sullivan, a New York Times article. The story claimed Clinton "suggested there was a link between the Qaeda franchise in North Africa and the attack at the American diplomatic mission in Benghazi, Libya."

"Well this is a stretch beyond what I said or intended, but I don't think we need to say more," Clinton wrote, adding, "Do you agree?"

Sullivan's response included harsh words for one of the reporters who worked on the story, Eric Schmitt.

"We are working with Schmitt, who is being a pain in the ass," Sullivan wrote.

In spite of his apparent annoyance with Schmitt, Sullivan added that he felt "okay about" the story. Schmitt declined to comment on this story.

Another message from October 11, 2012 featured Clinton's longtime adviser, Philippe Reines, describing an interview. The email was sent from Reines to Clinton and Tom Nides, who was her deputy secretary of state. In it, Reines mocked Wall Street Journal reporter Monica Langley's behavior during an interview with Clinton and said he had never witnessed "that behavior among any type of mammal."

"She moved that yellow chair as close as it went. Knee to knee. Amazed she didn't try knee in between knee. And if that wasn't enough, she leaned forward. More like a pivot, as far as her torso could fold forward to minimize the space between their heads. Was like the dental hygienist rolling around on the floor to get the best access to your mouth depending on what tooth she was trying to get access to," Reines wrote of Langley.

Reines continued by contrasting Langley's alleged behavior with other journalists who covered Clinton.

"I've never seen a Westerner invade her space like that. And even the non-Westerners I've seen do it based on cultural differences have been only briefly to greet. This went on like that for 51 minutes — unacceptable in any culture," wrote Reines, adding, "I don't even think you see that behavior among any type of mammal."

Reines concluded by indicating he really enjoyed watching Langley's interview with Clinton.

"The touching the leg and repeatedly calling her 'Hillary' was just gravy," Reines wrote. "But it was wonderful. One of the best interviews I've ever witnessed. Wish it were on live tv."

Nides clearly enjoyed Reines' dramatic narration of the interview.

"I may go throw up since I am laughing so hard," Nides wrote.

Langley did not respond to a request for comment from Business Insider.

Reines has become well known for his communications with the press. In March, he copied several reporters in a lengthy email exchange wherein he berated Gawker's J.K. Trotter for what he described as a "cockamamie theory."

Reines' most infamous exchange with a reporter was an expletive-filled argument he had with Buzzfeed's Michael Hastings on September 23, 2012. Hastings accused Reines of giving an "offensive" statement to CNN and offering "bulls---" responses to his questions. Reines responded by calling Hastings an "unmitigated asshole" and telling him to "f--- off."

The emails released on Friday included an apology Reines subsequently sent to Hastings on September 25, 2012. Reines began by noting the Benghazi attack caused tensions at the State Department.

"Hi Michael, As you can imagine this has been an intense time for everyone at the State Department, including me. While I stand by the fundamental principles at issue here, that does not justify my unprofessional response to your emails," Reines wrote. "I particularly do not want my words to be a distraction from this tragedy. I apologize, both for my language and for my tone."

Hastings responded with a note saying he appreciated Reines' email. He noted he once lost someone he "cared for very deeply" to violence overseas.

"This experience probably added to the intensity behind my questions and responses as well," Hastings wrote. "In the interest of diplomacy and extending an olive branch: we should get a drink sometime, off the record."

Reines did not respond to an email from Business Insider. Hastings passed away in 2013.

The approximately 300 emails released on Friday were the first installment of a rolling release of 55,000 pages of emails that was ordered by a federal judge. Clinton turned over the emails to the State Department from her private email server.

Clinton's use of a personal email address during her time as secretary of state has been heavily criticized by Republicans and others who suggest it may have violated federal regulations and prevented transparency. A spokesperson for Clinton did not respond to a request for comment on this story from Business Insider.

This story was updated at 8:36 p.m. to note Schmitt declined to comment.