Chris Rock is one of the greatest comic talents in the world, but when he arrived on Broadway to perform his first play, The Motherf***ker in The Hat, he did not yet know how to properly cross a Broadway stage. Rock says that his life has mimicked each role in the play—both the heart-breaker and the heartbroken—and he tells Alec that performing in the show was the hardest thing he has ever done.

When Herb Alpert started playing trumpet with his band Tijuana Brass, Woody Allen and George Carlin were the opening acts. In 1966, The Brass outsold The Beatles. Alpert went on to co-found A&M Records, where he identified and signed some of the industry's greatest talent: The Carpenters, The Police, and Cat Stevens. He and his partner sold A&M in 1989 for half a billion dollars. He says he’s looking for the same thing as everybody else—a life of purpose and meaning. 

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Chris Rock is one of the greatest comic talents in the world, but when he arrived on Broadway to perform his first play, The Motherf***ker in The Hat, he did not yet know how to properly cross a Broadway stage. Rock says that his life has mimicked each role in the play—both the heart-breaker and the heart-broken—and he tells Alec that performing in the show was the hardest thing he has ever done.  

When Herb Alpert started playing trumpet with his band Tijuana Brass, Woody Allen and George Carlin were the opening acts. In 1966, The Brass outsold The Beatles. Alpert went on to co-found A&M Records, where he identified and signed some of the industries greatest talent: The Carpenters, The Police, and Cat Stevens. He and his partner sold A&M in 1989 for half a billion dollars. He says he’s looking for the same thing as everybody else—a life of purpose and meaning.  

Kristen was in college when an Acting 101 class prompted a move to L.A. She had little experience, but a tremendous gift for improv, and she soon found herself in a room auditioning for SNL. Hundreds of personas later, Wiig is regarded by SNL creator Lorne Michaels as one of the three or four greatest SNL talents ever. Kristen’s expertise translated well to film, and she eventually won an Oscar nomination for her Bridesmaids screenplay. She joins Alec to talk about the arc of her career and the steps she hopes to take next.

Dick Cavett shares some of his memories with Alec: meeting Orson Welles in the lobby of the Plaza; talking with Marlon Brando by phone—“I was told he would [call] at a certain time and we talked with the sun about 15 degrees above the horizon until well after the moon had risen;” and interviewing Laurence Olivier in the Wyndham Hotel when Cavett says, he was feeling so depressed “I just want[ed] to go home and get under the rug.” Dick Cavett is the master of talk, a television legend; in this conversation, he shows Alec why his career has spanned nearly five decades.

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Kristen was in college when an Acting 101 class prompted a move to L.A. She had little experience, but a tremendous gift for improv, and she soon found herself in a room auditioning for SNL. Hundreds of personas later, Wiig is regarded by SNL creator Lorne Michaels as one of the three or four greatest SNL talents ever. Kristen’s expertise translated well to film, and she eventually won an Oscar nomination for her Bridesmaids screenplay. She joins Alec to talk about the arc of her career and the steps she hopes to take next.

Dick Cavett shares some of his memories with Alec: meeting Orson Welles in the lobby of the Plaza; talking with Marlon Brando by phone—““I was told he would [call] at a certain time and we talked with the sun about 15 degrees above the horizon until well after the moon had risen;” and interviewing Laurence Olivier in the Wyndham Hotel when, Cavett says, he was feeling so depressed “I just want[ed] to go home and get under the rug.” Dick Cavett is the master of talk, a television legend; in this conversation, he shows Alec why his career has spanned nearly five decades.

Billy Joel has sold more records than The Stones, Bruce Springsteen, and Madonna—though the “rock star thing” is something he can “take off.” Joel started playing piano when he was about four or five years old, but he admits that he doesn't remember how to read sheet music anymore. He says it’d be like reading Chinese. That doesn't stop the third best-selling solo artist of all time in the U.S. from plunking out a few tunes with Alec.

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Billy Joel has sold more records than The Stones, Bruce Springsteen, and Madonna—though the “rock star thing” is something he can “take off.” Joel started playing piano when he was about four or five years old, but he admits that he doesn't remember how to read sheet music anymore. He says it’d be like reading Chinese. That doesn't stop the third best-selling solo artist of all time in the U.S. from plunking out a few tunes with Alec.

READ | Interview Transcript

This week Alec sits down with comedian Jerry Seinfeld who debuted on HBO in 1981, the same year he first appeared on Johnny Carson. Jerry Seinfeld was 27 years old.

Seinfeld's material stood out. It wasn't about his upbringing or personal relationships. It was about our universal experience of small things. Eight years after his HBO debut, he and Larry David created a weekly series that changed both their lives. After Seinfeld ran for nine seasons, Seinfeld went back to stand-up, and to his audience. As he explains to Alec, Seinfeld feels uniquely connected to his fans: “You have this relationship with the audience that is private between you and them. Critics want to write, people want to talk. We have our own thing that nobody can break … once you build that it can't be broken by outside forces.”

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James Toback and Alec joined forces to make the documentary Seduced and Abandoned, which began as a story about raising money for a film. However, it soon became a study of the tension between art and commerce and how difficult it has become to secure financing for independent films. 

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James Toback and Alec joined forces to make the documentary Seduced and Abandoned, which began as a story about raising money for a film. However, it soon became a study of the tension between art and commerce and how difficult it has become to secure financing for independent films. 

Chris Columbus has brought to the screen some of the biggest American family films in the last 20 years: Adventures in Babysitting, Home Alone, and Mrs. Doubtfire. He also produced and directed the first two Harry Potter films and produced the third as well. Despite this success, Columbus admits that he “always, to this day, [feels] like [he’s] gonna walk on a movie and get fired.” He reveals to Alec what it was like working with brilliant improvisers like John Candy and Robin Williams—and casting Macaulay Culkin in Home Alone.

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