We start with Hewitt retelling his favorite joke as told by his friend Jan Luby. Jim actually snorts. We resume the interview from part 1, and Hewitt talks about his reaction to his listening of Utopia Revisited. Hewitt then shares a story of his part in the origin of Jim’s band name Jim’s Big Ego. As punishment, Jim plays another clip from Hewitt’s album, The Only Drowning Goldfish: I Will Crumble. Jim makes a pitch for Hewitt to release his songs to the world ‘for the love of humanity.’ Hewitt tells the story of how he left the Boston area and his personal and creative journey since then. He talks about coming back from chemotherapy and how he found joy in making music again after his recovery. Lionel draws parallels between Hewitt’s story and that of Phil Broikos who visited us during season one of our podcast. We talk about the role of religion in both Phil, and Hewitt’s creative journeys. Lionel reflects on his friend who has scored a number of songs and doesn’t know what he can do with his music, reflecting on our conversation with Dave Herlihy as well. Jim pushes back against defeatism in the face of the flood of free music out there. Hewitt talks about working with Jim Steinman before he passed. We talk about the effect of MTV on music and how lots of recording artists wouldn’t have been as successful without it. We also talk about the elongation of hits in the public eye because videos stayed popular longer than songs on the radio. Jim mentions a quote from Seth Godin: “people like us like things like this,” and the tribal aspect of letting viewers decide what they like. Hewitt talks about wanting to be surprised by music, which was more possible when bands put out a new record every year, rather than riding out an album for multiple years on MTV. Lionel talks about a time when Jim told him that monetizing music was dead and how he didn't believe it then, but does now. Hewitt talks about wanting to support the artist Matt Pond, and how he wished people would be patrons of music. Naturally, Patreon comes up. Lionel wishes there was a way to support artists with micro-donations on YouTube. Hewitt points out that there is a feature in live chats that works like this. He mentions Philip McKnight and his channel Know Your Gear, and how he has support buttons in his live chats. Jim breaks in to play clips from Hewitt’s songs but is derailed by Lionel asking about the naming convention used in the tracks he sent us. Hewitt explains that the secondary titles indicate the number of mixes. Jim plays clips from Evelyn, Howl, and Until the Sun Explodes. Hewitt mentions his friend, Christian Finnegan and his podcast Audio Spackle where he referred to Hewitt as “the Howard Hughes of music.” He talks about his plans to eventually get the music out there when they are ready. Jim pushes back, saying he should release the songs and work on the next ones. Hewitt also mentions how hard it is for new songwriters to be among peers who aspire to be artistic, rather than commercial. We mention Taylor Swift and how she is inspiring a new generation but how she lacks competition in this current environment. Lionel mentions how he's been turned on to Lana Del Rey and some other artists and talks about how he demonstrates how many new artists are copies of older artists, Lana being the main exception. He says that collaboration like the kind Jim engaged with, with Kurt Uenala is so important. Jim stresses the importance of open mics in honing the craft of the singer songwriter. He stresses the unpredictability of which song is good, and how the artist is often the worst judge of this. We end with a discussion of how good or great is relative, and Hewitt mentions a song for which we had no clip, called The Shame of Diamonds, which he felt achieved everything he wanted. We will leave that song for when he decides to release it.