"If I Weren't So Stupid, You Wouldn't Be So Smart"; "You Can Drink an Ugly Girl Pretty"; "If William Shatner Can, I Can Too" — these are just a few of the colorful tunes that Jeff Daniels has managed to pen and perform while not making films, starring in Broadway plays, running his Michigan-based theater company, or winning Emmy Awards for his role as newscaster Will McAvoy in Aaron Sorkin's new HBO series The Newsroom.

Finding himself in between shooting schedules for the upcoming Dumb and Dumber sequel and season three of The Newsroom (though still maintaining his shaggy Harry Dunne haircut), Daniels has decided to take his vocal chops, guitar picks, and diary of storytelling songs to New York audiences in six performances at 54 Below. TheaterMania sat down with the actor/singer/songwriter, who offered a look inside the evolution of his music career from his early days in a high school production of South Pacific to his auspicious nights as a club singer, shooting down hecklers with some of Robin Williams' most treasured one-liners.

(Warning: If you haven't finished season two of The Newsroom, a spoiler awaits at the end.)

Jeff Daniels
Jeff Daniels
(© David Gordon)

Most people find the intimate setting of 54 Below to be one of the most intimidating places to perform, but you seem right at home. Is this your natural habitat?
When I first started playing guitar in front of people I was in a flop sweat. I had no idea what terror was for a performer. I could be on a stage off-Broadway or even on Broadway and it was just like home. But put a guitar in my hand— It took a while to figure out how to make that your friend and how to use it. Now I prefer it to a five-hundred- or seven-hundred-seater. You really get to talk to and sing to them. [And] you don't have to push as hard. They come to you versus you having to go out to them.

I know you like to talk to your audiences and I'm sure they like to talk back. How do you keep the hecklers under control?
You use some of the standards: "I remember my first beer." [There was] a woman the other night [heckling]. I used Bette Midler's, "They paid to hear me, not you." I think Steve Martin's got a good one: "Oh, you're what happens when cousins marry." Robin Williams told me that one [actually]. I said, "give me five guaranteed heckler kills." That was one of them.

Are there still people who are surprised to see you singing and writing songs?
Yeah, there are certainly people that have no idea and I really don't care. I do it because I enjoy it. I can see doing it in clubs when I don't want to act anymore. I'm lucky I don't have to do it for a living like a lot of the pros out there…For me, it's just sheer enjoyment.

Which came into your life first — music or acting?
I was singing in [the] high school choir and the teacher was also the musical director. She grabbed anyone in the small-town high school choir who could sing and put us in South Pacific because she needed guys. I instantly knew how to get laughs during "There Ain't Nothin' Like a Dame." I had like two lines…But I improvised some stupid knee-slappy dance and she cracked up. She had me do it three times in the audition. Later on, she had me play Fagin in Oliver, Harold Hill in Music Man, El Gallo in The Fantasticks, Snoopy in Charlie Brown. She just would do plays built around me and three or four other people, so by the time I was twenty, I had done easily ten or twelve musicals.

If your introduction to music was through musical theater, when did you start playing guitar and singing and writing in the style you do now?
I played piano in high school. I wanted to be Elton John and I kept having to play songs that weren't Elton John's so I quit, [but] I bought a guitar in 1976 when I moved to New York. I guess that was me saying I want music to stay in my life somehow and this is mobile and I can take it anywhere and I have a feeling that I'm going to be sitting in my one-room apartment waiting for the phone to ring for months. It became my great friend. In a way, music and the guitar helped keep me sane while I was struggling on my way up.

If your character on The Newsroom, Will McAvoy, were to write a song for his fiancée, MacKenzie, what would it be called?
Well, it depends. Before or after the ring?

Before.
"You Know Me Better Than I Know Myself and I Hate You For It."