Gross has won praise over the years for her low-key and friendly yet often probing interview style and for the diversity of her guests. She has a reputation for researching her guests' work largely the night before an interview, often asking them unexpected questions about their early careers.
Gross began her radio career in 1973 at WBFO, a public radio station in Buffalo, New York, where she had been volunteering. In 1975, she moved to WHYY-FM in Philadelphia to host and produce Fresh Air, which was a local interview program at the time. In 1985, Fresh Air with Terry Gross went national, being distributed weekly by NPR. It became a daily program two years later.
The San Francisco Chronicle wrote that Gross' interviews are "a remarkable blend of empathy, warmth, genuine curiosity, and sharp intelligence." Gross prides herself on preparation; prior to interviewing guests, she reads their books, watches their movies, and/or listens to their CDs. The Boston Phoenix opined that "Terry Gross … is almost certainly the best cultural interviewer in America, and one of the best all-around interviewers, period. Her smart, thoughtful questioning pushes her guests in unlikely directions. Her interviews are revelatory in a way other people's seldom are."
Gross has drawn added public attention following some occasions when interviews have taken a confrontational turn. Four notable examples are:
The February 4, 2002, interview with Kiss singer and bassistGene Simmons began with Gross mispronouncing Simmons' original Hebrew last name. Simmons dismissively replied to her that she mispronounced it because she had a "Gentile mouth"; Gross responded that she is Jewish. She went on to question Simmons' views on the importance of money. In the interview, Gross begins a question, "So having sex with you," to which Simmons interjects, "You're going to have to stand in line." Gross questioned Simmons about his many liaisons. Later Simmons said, "If you want to welcome me with open arms, I'm afraid you're also going to have to welcome me with open legs," to which Gross replied, "That's a really obnoxious thing to say." Unlike most Fresh Air guests, Simmons refused to grant permission for the interview to be made available online on the NPR website. The interview appears in Gross' book All I Did Was Ask, and unauthorized transcripts and audio of the complete original interview exist.
An October 8, 2003, interview with Fox News television host Bill O'Reilly, who walked out of the interview because of what he considered were biased questions, creating a media controversy fed by the ongoing presidential campaign. Toward the end of the interview, O'Reilly asked Gross if she had been as tough on Al Franken, who had appeared on the program two weeks before O'Reilly. Gross responded, "No, I wasn't ... we had a different interview." Gross was later criticized by then NPR ombudsmanJeffrey Dvorkin for "an interview that was, in the end, unfair to O'Reilly" and that "it felt as though Terry Gross was indeed 'carrying Al Franken's water'." Dvorkin described Gross' interviewing tactic of reading a quote critical of O'Reilly after he had walked out of the room as "unethical and unfair". Gross was later supported by an NPR colleague, Mike Pesca, who contended that O'Reilly did have the opportunity to respond to a criticism that Gross read to O'Reilly levelled by People magazine, but that he defaulted by prematurely abandoning the interview. On September 24, 2004, Gross and O'Reilly met again on O'Reilly's television show in which Gross assured O'Reilly "that no matter what you ask me, I'm staying for the entire interview."
A February 9, 2005, interview of Lynne Cheney, conservative author and the wife of then–US Vice PresidentDick Cheney. The initial focus of the interview was on Cheney's latest history book, but Gross moved on to questions about Cheney's lesbian daughter Mary and her opinion of the Bush administration's opposition to same-sex marriage. Cheney declined to comment on her daughter's sexuality, but repeatedly stated her opposition to a constitutional amendment banning same-sex marriage, which was being endorsed by President George W. Bush. Cheney declined to discuss the matter further. Later, when Gross brought the interview back to issues of gay rights, Cheney again refused to comment. According to producers, Cheney had been warned that Gross would be asking about politics and current events.
A June 2014 interview of Hillary Clinton, in which the former Secretary of State and potential 2016 Presidential candidate was questioned about her shifting support for same-sex marriage and whether her changing opinion was a political calculation. When Clinton answered that her view on the issue had "evolved", Gross pressed for a more detailed answer. This led to a tense exchange in which Gross explained that her persistent questions were an attempt to "clarify" Clinton's reasoning for the shift in her viewpoint, and Clinton responded "No, I don’t think you are trying to clarify. I think you are trying to say that I used to be opposed and now I am in favor and I did it for political reasons. And that’s just flat wrong."
Gross was married early on in her life, but was in divorce proceedings by the time she started her radio career in 1973. She is now married to Francis Davis, jazz critic of The Village Voice. The couple reside in Philadelphia. They have no children, and in an interview with B. D. Wong, Gross said this is a deliberate choice on their part.
Gross wrote in the introduction to All I Did Was Ask: Conversations With Writers, Actors, Musicians, and Artists that she is sometimes asked whether she is a lesbian, due to short hair and the number of gay interviewees on Fresh Air. In her interview with Rubin "Hurricane" Carter, she mentioned that she had lived in a commune.