David Letterman's Iconic Interviews With Women

Yet another titan of the late night talk show circuit has marched gently into that good night. America's surliest talk show host David Letterman has officially retired as Late Night host, and his final show was a hilarious, star-studded sendoff. There's a lot lost in his absence; beyond the Top 10 Lists and Paul Shaffer banter, the 68-year-old's reputation for being insufferably frank and refusing to suck up to his guests made him one of the best interviewers in late night television. While some guests have left feeling more alienated than others (he really let Paris Hilton have it), the best of them have played along with Letterman's "crotchety uncle" routine and shot it right back at him.

His brusqueness ruffled quite a few feathers (both Cher and Madonna have cursed at the man on air for being a little too sassy), but. after 33 years, he built one endlessly entertaining rapport after another with numerous pop culture icons, the most infamous of which were often with women. His impressive roster of long-time regular guests included Sarah Jessica Parker, Julia Roberts, Julia Louis Dreyfus, and even Cher (once they apologized to each other and made up). In fact, most of us born after 1985 might not even realize just how many fascinating and funny ladies Letterman has had iconic interviews, feuds, and friendships with throughout the years.

Now that the talk show host has bid his adieu, I want to celebrate his most awkward, antagonistic, and downright hilarious interviews with some of America's most famous and infamous women. Here are seven of his best moments.

Madonna

While it's still not totally clear what was happening in this interview, it would seem that Letterman offended Madonna before she came out onstage by making a joke about her sex life. The pop star then went on air, eluded all of Letterman's questions with hostile responses, dropped 14 f-bombs, starting smoking a cigar, and refused to leave the stage after the commercial break. Iconic.

Paris Hilton

Oh dear, he did not like Paris Hilton. Not only did Letterman refuse to stop bringing up her stint in prison, but he repeatedly asked the hotel heiress and fashion icon to think about the legacy she was leaving behind for young people. When Hilton told him that he was making her sad, he apologized and offered to buy her a parakeet. Oof.

Lindsay Lohan

Letterman pulled a similar stunt on Lindsay Lohan, pressing in hard about her rehab stints and problems with the law. Like Hilton, Lohan admitted that the questions were making her feel awkward; unlike Hilton, she stood up to the talk show host and got in her fair share of one-liners, coming across as legitimately self-aware, repentant, and funny.

Drew Barrymore

Lest we forget, Drew Barrymore was America's favorite wild child in the early '90s. Her fun and carefree energy paired hilariously with Letterman's grumpy clown schtick, and the two had wonderful chemistry together. Not a week after Madonna's interview, Barrymore offered to celebrate the comedian's birthday with a strip tease on his desk that ended with her flashing him.

Julia Louis-Dreyfus

Letterman treated some guests like toys, and others like peers. Julia Louis-Dreyfus fell firmly in the latter category. Never one to put up with guff, the Veep actress was a formidable opponent for Letterman's off-the-cuff sass. After John McCain famously stood up Letterman with a lie about having to return to Washington, when in fact he had an interview with Katie Couric, Louis-Dreyfus went on the show and joked that she had intentionally scheduled an interview with Couric to conflict with her Letterman appearance to get back at them for the affront. "She's just gonna be sitting their waiting!"

Sarah Jessica Parker

Letterman just couldn't help but make fun of whoever sat in the big comfy chair next to his desk, and even Carrie Bradshaw herself felt the sting of his wit. Fortunately, Sarah Jessica Parker has seen many a rodeo, and she knows how to take a joke. Try as he would to needle her about some of her more outlandish fashion choices over the years or the overt sexuality of her hit HBO show, Parker stands by the designers behind the clothes, and the choices behind the show, while poking a little bit of fun at both. In the above interview, Letterman makes a joke about a character death in the then-upcoming Sex and the City movie; Parker one-ups him, jokingly admitting to the audience that, actually, all four women die in the first ten minutes, "but the next four women are amazing! So young and luscious!"

Cher

Since the beginning of the show in 1982, Letterman had been trying to coax Cher into coming onto the show. When she finally made an appearance in 1986, she made national news by calling him an "a**hole," and telling him he was mean to his guests. The 17 minute long interview is tense and hilarious as an uber-intimidating Cher toys with a nervous and giggling Letterman. The two eventually made up, Cher became a regular guest on the show, and, by later interviews ,it was clear that the two were old friends.