I've played some shows that were pretty tough. Mainly because you get 6 hours of rehearsal during the day (for a 3 hour show), then you have to play the show that night.
Wicked was, well...wicked. Five string, fretless, and upright. Completely written out, non-idiomatic fills that span 2 and a half octaves, exposed Jaco-istic parts on fretless, arco upright, odd meters, there's a tune that alternates between 5/8, 2/4, 6/8, and 4/4...
West Side Story some gnarly parts, and odd phrases. I don't think Bernstein played the bass.
Les Miserables hard (for me) because it's very operatic, tempos constantly change. If you take your eye off the conductor, you're toast.
When I was in college, I was in a small group that consistently pushed me. We also played Zappa's "Echidna's Arf", as well as "Joe Frazier" and Return to Forever's "After the Cosmic Rain" & "Majestic Dance".
I assume that you played Wicked when the national tour rolled into town. I'm surprised,given the complexity of the score, that they use local players and not a dedicated bassist on the tour.
I know what you mean about those six hour rehearsals then the show. While not a national tour, I played a show of Jason Robert Brown music last week, that featured Solea Pffiefer (I saw her in the 20th anniversary production of Songs For a New World at City Center a few years back- Jason Robert Brown sat in and played the second act) with a group of very talented college students. Due to a mix-up by the MD, I only got the 237 pages of piano/conductor score on Monday. Tuesday was the rehearsal, Wednesday was the show. I had copies of the bass books of the shows that I had played before - Songs For A New World, Last Five Years and Parade - but didn't have time to compare most of them measure by measure to the p/c scores. Then there were songs from Bridges of Madison County, Honeymooning Las Vegas, and Mr. Saturday Night. The orchestra parts for the last two are not commercially available yet. I ended up having to read from the p/c scores. I hate having to transpose up an octave while also trying to pick out what parts are mine on the fly! The concert did go very well, and Solea was amazing!