From Jennifer Aniston turning down Lorne Michaels to Lindsay Lohan dishing on her exes 2019 was another stellar year for the shock jock.
He's a shock jock who has recently discovered his more sensitive side.
And while Howard Stern has expressed his regrets and charted his growth in his new memoir, "Howard Stern Comes Again," he hasn't lost his touch as a penetrating interviewer.
Below are some of his greatest moments from 2019.
K-Stew Didn't F--k Rupert Sanders
Kristen Stewart opened up like never before about her 2012 romantic tryst with director Rupert Sanders, which reportedly led to her split from Robert Pattinson and Sanders' divorce from then-wife Liberty Ross.
"I did not f--k him. This is like the most candid interview," the 29-year-old actress told Stern on his SiriusXM radio show in early November. "No, I didn't f--k him."
When Stern asked his guest why she didn't scream that from the mountaintops after being photographed making out with her "Snow White and the Huntsman" director while she was dating her "Twilight" co-star and Sanders was married to Ross -- who was also in "Snow White" -- Stewart said, "Well, who's going to believe me? It doesn't even matter."
"It looked like... You know, you make out with a dude in public, it definitely looks like you did [have sex]," she said, admitting, though, that the fling "wasn't innocent."
Stewart's main gripe is that she was denied a role in the 2016 sequel, "The Huntsman: Winter's War," and she chalks it up to the scandal.
"We lived in a different time then, you know what I mean? I feel like the slut-shaming that went down was so absurd," she explained. "And they should've put me in that movie! It would've been better. Not to be a dick, but... They didn't put me in that movie because I went through such a highly publicized scandal, and so they were like scared of touching that."
Stern noted that was a "dumb move" by the studio, and Stewart agreed.
Howard Asks Demi Moore Some Very Real Questions About Her Book
While much of the stories in the press about Demi Moore's tell-all book, "Inside Out," earlier this year focused on the dirty details of her marriages to Bruce Willis and Ashton Kutcher, Stern asked about nearly everything but those two exes when she appeared on his radio show in October.
Instead, he spent a large chunk of time asking Moore about her troubled childhood, being raped as a teenager and the affect both of those had on her life going forward.
It's a great interview and you can read a full breakdown here.
Why Jennifer Aniston Saw a Shrink
Jennifer Aniston told Stern, in yet another disarmingly candid interview, she visited a psychologist after her divorce from actor Justin Theroux to help process the split after her ex was pictured spending time with multiple actresses and models. The former couple, who tied the knot in 2015, split in late 2017 after two and a half years of marriage. They announced their separation that following February.
She also revealed she turned down a very big show before she joined "Friends" in 1994: "Saturday Night Live." According to Aniston, "SNL" creator Lorne Michaels approached her multiple times about joining the sketch-comedy series.
Although she was "thrown" over Michaels even considering her to be on the show, Aniston turned the gig down, boldly telling Michaels "SNL" seemed like "such a boys club" and suggested the women on the show should have been "treated better."
"You're just not the brightest in your early 20s," she admitted to Stern.
Lindsay Lohan Gets Real About Her Relationships
Stern grilled Lindsay Lohan about her romantic past back in January... it was gold.
The shock jock first mentioned Wilmer Valderrama, who she dated back in 2004. Calling him the "first" of her boyfriends, she went on to call him "a good guy." Stern, of course, also pointed out that he's "so f--king good looking," something she didn't deny.
He later asked about her relationship with Samantha Ronson, who she began dating in 2008. The coupling made headlines at the time as the DJ was the first woman Lohan dated in the public eye.
"I talk about that on the show," said Lindsay. When asked if it was "painful" to revisit by Howard, Lohan said, "No, we're friends more than anything. We were always more best friends."
One of her VIP "ambassadors" on the show is bisexual, she explained, adding that she "comes to his defense a bit" during an upcoming episode. "They shouldn't be passing any judgment," she added of his costars.
"I was the first one who was like, that came out about it, really, for my age," she continued. When asked why people were so "angry" about her own relationship back in the day, she added, "It was weird."
Stern also asked about the "great love of her life," though she refused to name names about who it was. "It was years ago, I can't say his name. It's no one famous," she said. Lohan played it coy about why they split, but added, "He lied about two things. It was something serious. When you're with someone for four years, that's a little too long to hold a lie."