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Like quite a few Americans, I tuned in the other night to the new Jay Leno Show, curious to see what Kanye West would say about interrupting Taylor Swift's acceptance speech for winning best Female Video for "You Belong With Me" at the MTV Video Music Awards.  According to Rolling Stone, Swift was seen "hysterically crying" backstage and West was bounced from the show.  Now a day later, there was Kanye slumped in an oversize chair sitting opposite Leno ready to discuss the incident.

Watching the interview made me think back to the recent interviewI shot with Leno for his website promoting my memoir Big Sid's Vincati.. Because of my own experience, I could recognize some of Leno's characteristic moves as interviewer. Perhaps because critics were already calling the Kanye West interview another "Hugh Grant moment," Jay begins graciously, thanking the rap star for not backing out.

Then Leno asks his first question: "Tell us about your day, have you had a tough day, today?"  Leno chuckles through the line and the audience amplifies the laughter.

But Kanye's response is totally absent of humor.  Characteristically, Leno persists, feeding Kanye another opportunity to lighten up.  Jay says, "When did it strike you-uh oh...!"

And again the audience follows Jay's lead and laughs, and this time so does West, who smiles as he admits, "Soon as I gave the mic back to her and she didn't keep going . . . !"  Collective laughter results.  This is the high point of the segment. Encouraged, Leno now goes for broke: "I was fortunate enough to meet your mom a number of years ago . . . what do you think she would have said about this?"

The line of questioning may have surprised some, but not me.  My book, Big Sid's Vincati, is about building a one of a kind motorcycle with my dad.  I had used our story to explore the inevitable difficulties that color all relationships between parents and their kids.

When I was filming with Leno, he dwelled on the scenes in my book that explored the painful experiences-the fights, the things you say that you wish could you take back but know you never can.  In talking with me and my dad about the book, Leno observed, "Its that classic thing that goes back and forth  ...  that's the real dynamic that makes Big Sid's Vincati a fascinating read."

Then Leno did with me what he does best-sharing his own experience: "My dad was a street kid, a prize fighter!" adding,  "Luckily, I was stupid, like him, so we had stuff in common, unlike you guys." 

I laughed when Leno said this to me, but I was also moved at his ability to display his vulnerability.  This openness is what enables Leno to connect to his audience and it is also his best strength as a comic.  It is an example of how comedy can help you say stuff you couldn't otherwise say, and feel better for having said it.

So when Leno brought up Kanye's mother, I knew exactly what Jay was doing. Most of us can look back over our lives and identify some person-usually a mom or a dad--who raised us and made us who we are.  Jay wanted Kanye to chuckle and think back, then tell a story about getting bent over his momma's knee, or sent to his room, something that would allow him to understand that in the grand scheme of life, this too shall pass.  We may not all be celebrities but we could all have understood that. 

But Jay had miscalculated. Kanye's mother Donda had died unexpectedly in November of 2007. In response to the question, Kanye drew quiet and looked dazed, as if his mother's ghost suddenly appeared before him there on stage. Then for a moment West cried, and Leno reached over and patted him on the knee, before saying, "Hey, you ready to sing? Give it a shot?"

So it didn't all go as Leno scripted it.  The laughs never quite materialized, but I think West's hurt was real. Leno is rarely praised for his skill as an interviewer and that's a pity.  I certainly came away with a new respect for Jay after our conversation about my memoir. His blend of comic integrity is disarming and when practiced on the right guest, it can make for memorable entertainment, as it did the other night with Kanye West. Now we all get to see if Leno can keep it up.

Matthew Biberman, Big Sid's Vincanti, motorcycle, memoir, Penguin Books