Little Gray Books
The "Little Gray Books were a series of lectures, hosted by John Hodgman, from 2001 to 2006. They represented Hodgman's attempt to create a "radio program on stage", and were named in honor of the 1920s collection of pamphlets Little Blue Books, one of which John's mother gave him when he became a literary agent (#1143, "How to Prepare a Manuscript"). Jonathan Coulton served as the musical director for these lectures, performing many originals that would later be released as Other Experiments or reproduced for Where Tradition Meets Tomorrow or during Thing a Week.
The themes of the lecture series were titled as if they were a similar series of useful How-To booklets with charmingly archaic titles.  Each Little Gray Book program loosely followed that theme and featured a selection of guests. These lectures included readings by authors, novelty demonstrations, comedy and music. Most of the Little Gray Book lectures took place at the Galapagos Art Space, in the Williamsburg neighborhood of Brooklyn NY.
Jonathan's role has been described in this way: "The loyal audience, which Hodgman has built, anticipates the closure Coulton’s songs often bring. They have the uncanny effect of wrapping-up and summarizing the night’s theme in well-crafted song. Hodgman believes, 'it is unconscionable that no one has found a way to make one million dollars off his talents yet.'"
The only nearly-complete recording of a Little Gray Book lecture currently available on the internet is the one made of Lecture 29, on the topic of radio.  The lecture took place in Philadelphia, in order to take advantage of radio-quality sound recording at the Indre Studio.  However, recordings from a total of seven of the lectures were at repackaged and released as podcasts. These podcasts were compiled by Jonathan Coulton and John Hodgman and bookmarked with inventive fictional settings and events as described by the two of them. Each podcast reprised readings, songs, or amusing happenings from one specific past lecture.
Several of Jonathan's songs were written for the lectures or the podcasts, including Skullcrusher Mountain, The Future Soon, The Presidents, and Brookline, the last of which was prompted by the lecture about Hodgman's hometown of Brookline, Massachusetts.
The lectures were:
|1||How to Begin an Important Project ||none|
|2||Hints on Public Singing||I'm So Lonesome I Could Cry, Rainbow Connection|
|3||How to Spell Several Common Words||none|
|4||How Can We Possibly Go On? (post- 9/11)||none|
|5||How to Win a Fight||none|
|6||How to Choose (or Make) the Perfect Gift||none|
|7||Secrets of Self-Improvement||none|
|8||How to Throw a Curveball||none|
|9||Mystery Cults of North America||I'm a Mason Now|
|10||How and When to Tell a Lie||none|
|11||Europe vs. America||Over There|
|12||Great Rivalries in American Spelling||none|
|13||How to Seek Your Fortune||none|
|14||How to Speak with Strangers||Don't Talk to Strangers|
|15||How to ReDistribute Wealth and Joy||none|
|16||How to Pour the Perfect Werthmann ||Mandelbrot Set|
|17||How to Generate a Winning Character||none|
|18||What Will Happen in the Future? (Full mp3)||The Future Soon|
|19||Exiles of Chicago||none|
|20||How to Negotiate All Kinds of Deals and Contracts||Screwed (demo)|
|21||How to Measure Misunderstood Genius||Skullcrusher Mountain|
|22||How to Gamble and Win (Full mp3)||Gambler's Prayer (demo)|
|23||Brookline: the Town that Has Everything Yet at the Same Time Has Nothing ||Brookline (demo)|
|24||Strange Gifts from Far-Off Lands ||none|
|25||The Animals: Are They Our Enemies?||I Crush Everything|
|26||Secrets of the Secret Agents||none|
|27||How to Lead a Double Life (or Death)||Dance, Soterios Johnson, Dance (demo)|
|28||(Title currently unknown)||none|
|29||How to Communicate Without the Aid of Wires||Calling Occupants of Interplanetary Craft, Dance, Soterios Johnson, Dance (new lyrics), Sweet Information|
|30||How to Observe President's Day, Observed||The Presidents|
|31||How to Commit the Perfect Crime||One More Score|
|32||How to Prepare Manuscripts for Publication ||Baby Got Back, Big Rock Candy Mountain|
Lecture #33 is listed as "How to Rest Quietly". It is technically not a lecture, but the title of the hiatus announcement found currently on the Little Gray Book Lectures website.