Last week I witnessed a landmark moment in culture: Spike Lee and Fran Lebowitz having a conversation. The moment was made possible by director Martin Scorsese’s production company who was filming the pilot episode for his new HBO series “Guest Host” based on his 2010 documentary “Public Speaking.”

The original documentary follows the caustic New York writer as she struggles with her perpetual case of “writer’s blockade” highlighting her unique take on modern life. The talk show seems to be structured in the same vein with a different host each episode interviewing Lebowitz, to extract more witticism from Lebowitz from different perspectives.

With no script or no planned dialogue, noticeable from the sometimes awkward pauses and Lee literally saying, “So what do we talk about now?”, the show goes beyond a classic “Inside the Actor’s Studio” forced diatribe, manifesting a natural conversation between two skilled artists at their crafts. It feels more like a caged lion match with two would-be guests carrying on a conversation instead of one owning the interviewer role firmly, but that might be because Lee is a forceful personality who does not shy away from stating his opinion, perhaps the other taping with Olivia Wilde went differently.

However, this show is not trying to replicate that Jay Leno-actor dialogue; just as Scorsese weaves a fierce stichomythia of wits into his classic films, here he is providing the set for it to happen naturally by placing the two powerhouse personalities in contact with each other. Watching it happen felt like it was one those crazy scenarios games like “what would happen if you put Abraham Lincoln and Paris Hilton in a room together?” Of course Spike Lee Fran Lebowitz aren’t so far-fetched a pairing, since both reside in their beloved New York City and share a very distinct point of view on the modern world, but it was clear from their conversation that their differences are quite strong.

The two caricature New Yorkers did less conversing and more talking AT each other, spending a majority of the 30-minute segment squabbling about the importance of sports in our society. Lee’s opening question: “Kobe Bryant or Lebron James?” was greeted with a chuckle from Lebowitz and a simple “I hate sports.” Immediately, the audience realized they were not just watching a casual talk show, but a vicious fight (perhaps similar to a Mohammad Ali fight which Lebowitz claims to have experienced first hand at Madison Square Garden—to Lee’s astonishment and chagrin, he immediately shot back “But boxing is a sport!”) between cultural icons who have become famous due to their bombastic opinions.

Lee, known for not aiming to please the audience with his controversial films, has been challenging society and culture since “She’s Gotta Have It” first came out in 1986 and continues today with the highly contentious “Red Hook Summer” that premiered in Sundance this year to unfavorable reviews. He’s a guy who knows what he likes and is going to make it and say it regardless of what people will think. This is exactly why it was immensely entertaining to watch Lee feel appalled and shocked by the even more matchless comments coming from Lebowitz. It was a challenge.

“But, watching sports is the great American past time! Do you hate America?” interrogated Lee leaning over his seat in bewilderment, to which Lebowitz retorted, “I don’t hate America, I hate sports.” The banter continued for 30 minutes revealing all sorts of unknown facts, like Lebowitz once danced with Michael Jackson at a party, and –not surprisingly- would never watch the Superbowl, even though it’ll be in her very own NY.

The conversation eventually felt situated in revealing a passion and ownership over this city in different ways, with Lee becoming almost a part of the city’s teams (we can all remember when he was blamed for the Knicks home-game loss during the 1994 playoff series) and Lebowitz coming across as protective of the city like a parent trying to preserve the virtue and dignity of their child. She doesn’t know what that new rectangular music-playing device thing is yet (ahem, iPod) but Mr. Scorsese did gift her a portable DVD player, perhaps to watch the countless number of classics filmed in her very own Woody Allen-esque version of the city.

The show ultimately fits in perfectly with Scorsese’s repertoire of work, chronicling another little piece of what makes New York that strange city where people can just be.