Stuck for a book, I picked up a copy of Callahan’s Key at the library, having seen Spider Robinson’s name mentioned a few times around here and being in the mood for some new SF. This shit is great: I haven’t had so much fun with an author since I discovered Kinky Friedman. Question is, there’s obviously a hell of a lot of backstory here: where should a neophyte begin, and are there any particular recommendations?
The first Callahan book is Callahan’s Crosstime Saloon
Then, (I think in order):
Time Travelers Strictly Cash
Callahan’s Secret
" " Legacy
" " Key
" " Con (This one I know nothing about…Key was the last one I read.)
There are also the Lady Sally books, about the bordello run by Callahan’s wife, Lady Sally. IIRC, they both neccessarily happen before Secret, although I’m not sure where they fit into the publishing timeline.
Callahan’s Lady
Lady Slings the Booze
The Callahan Touch fits between Secret and Legacy. The first three books, and I’m not sure how much of the second two, originated as magazine short stories in a common setting.
Spider suffers from Doc Smith’s Syndrome: “Now that you’ve destroyed the entire Universe, Doc, what are you going to do for a sequel?” 
The Callahan books are one of those series that has (have?) to be read in order.
The Callahan Chronicals is an anthology of the first three books. Off the Wall at Callahan’s is basically cut from the same cloth as Quotations from Lazarus Long – wisdom, wit, and humor from Spider and his Callahan’s-series characters, including a couple of filk songs.
His other work includes:
Telempath – his first book, and a one-off. He’s done better since, but it still stands up well as a first novel. A young man sets out to avenge his father and mankind after civilization is destroyed by the Hyperosmic Plague.
Mindkiller and its pseudo-sequel Time Pressure, mildly revised and joined as Deathkiller, and its sequel Lifehouse. Again it needs to be taken in order.
Night of Power – another standalone. Black Americans revolt and declare Manhattan an independent nation; a mixed-race couple is caught in the middle of it.
Stardance and sequels Starseed and Starmind. Zero-G modern dance and how to heal broken souls.
The Free Lunch – first book in a series, or I’ll eat Long Drink’s night watchman’s hat. A 12-year-old boy and a midget save the world from benevolent time travelers and malevolent capitalists inside a theme park.
Spider has also issued 1.43 shitloads of short story collections, many of which recycle previous ones (including the non-Callahan’s content of TTSC.) Bits and pieces of various novels are found in these. (“God is an Iron,” Kill the Editor, etc.) I have no great desire to try to sort what includes which parts of what else here.
I loved “God is an Iron”. Also love the Callahan books, though I’ve only read up to Key.
I hope it is – since it ends on a “to be continued note” – but I’m not optimistic. At the 2003 Worldcon in Toronto, when Spider was signing autographs in the hucksters’ room, when I got to the front of the line I got down on my knees, bowed my head, held aloft my copy of The Free Lunch and pleaded, "Sequel! [whimper] Sequel!" Spider only muttered and moaned, “I don’t wanna spend time in Thrillworld!” Jeez, man, you knew the assignment was dangerous when you took it!
The question with Robinson isn’t where to start, it’s where to stop. The man repeats himself so much you’ll eventually find yourself unable to tell if you’ve read one of his stories or not. At that point, you can stop actually reading his new work, safe in the knowledge that you’ve already read everything he’s going to write.
I finally read “Very Bad Deaths” after hearing Spider read the first chapter aloud at Necronomicon 2004 in Tampa. Good stuff, and sets up for a sequel. Sort of a thriller, with a crime solved by a trio consisting of a widowed newspaper-columnist, a female Mountie and a telepath.
I have noticed this (coincidentally, I’ve been working my way through the Callahan’s Chronicals audiobook the last week or two and have been enjoying it greatly), but it’s explained at the beginning of the book that the stories were originally published in sci-fi mags, and years apart from what I’ve gathered. He had to work in exposition so people weren’t totally lost, and specifically noted the challenge of doing so without being too redundant.
I’d never heard of Spider Robinson before starting the Chronicals, and I’m very glad I did pick it up. He’s inspired me to new heights of punnery. 
Very Bad Deaths freaked me out. Absolutely wonderful book. I listened to it and all the Callahan’s books a few months ago, from Audible. Great stuff.
Many thanks. Looks like my summer reading is sorted out for a while.
I read it and wondered – a guy who can think up stuff this horrible doesn’t want “to spend time in Thrillworld”?!