Stephen Sondheim had been successful (and not) on Broadway for over a decade before Company [Wikipedia]. In a lot of ways, it redefined “musical”, being less about a straightforward plot and more about emotional honesty and development. One major (and majorly entertaining) performance was a 2011 New York Philharmonic concert production [2h25m], with Neal Patrick Harris, Stephen Colbert, Jon Cryer, and Patti LuPone (amongst others). But, if you like comparison/contrast studies, there are others!
Let’s first look back to the original production [Playbill photo slideshow and article]. There was no filming of the original production, but this famous documentary about recording the cast album [52m] is really pretty great. The documentary also has commentary by Elaine Stritch and Hal Prince, if you like that kind of thing. Finally, the original cast came back together for AIDS charity performances in 1993 (23 years after opening). This was never filmed, but rehearsals were [1h], and they are interesting. (Beth Howland does “Getting Married Today” in the original key and tempo!) Here is a 35 minute compilation from that show.
There is also a 30 minute compilation of the 1995 Broadway revival.
The 2006 revival (reimagining!) starring Raul Esparza and Barbara Walsh [2h11m] won the Best Musical Revival Tony in 2007.
Currently we are awaiting the much-pandemic-delayed Broadway opening of the London revival, which has gender-swapped Bobby for Bobbie, and has other changes to be more sexuality and gender inclusive. Possibly happening very late this year!