Just happened across this thread - I delivered for Gumby's for the better part of '98 to 2001. Here's some random BS for ya...
Super cool place to work, made several friends there, some I still talk with to this day. Jason does still run the place (in its new location) - nice guy, great boss, took care of his people (and put up with a lot of **** from us and some customers, too).
Can't say about now, but back then...
- Gumby's closed at 3:30 AM Wed - Fri, and that meant someone could call and order up until 3:30 AM. I think the latest I ever delivered a pizza was 4:30 in the morning. The night shift started at 6 PM.
- It wasn't uncommon to get beers for tips. We would usually stash them throughout the shift in the walk in cooler. Occasionally someone would offer up a couple of hits from their bong.
- After 2:30ish in the morning, sometimes you would knock and knock, and you knew the person was there, but just passed out. I walked into someone's apartment once late at night/early morning - the window shades were opened, lights on, and I could see the guy passed out on his couch, and there was a check on the coffee table. I walked in, set the pizza down, grabbed the check, and left. LOTS of people paid with checks back then, rarely credit cards.
- I knew every apartment complex, how the buildings were numbered, etc. I didn't get my first cell phone until probably 2000 or 2001 - it made the job so much more efficient. I bet delivering with a smart phone makes the job way easier these days.
- I would typically put 100 miles on my car each night shift.
- You stank like dough and pizza sauce and sweat at the end of the shift.
- The Corps folks tipped the worst (if at all), considering you usually brought their pizza directly to their 4th floor dorm door - they were the only dorms that were 'open' back then - you didn't need a card or anything for access. Other dorms you had to walk up, call, and wait.
- Everything at Gumby's was fresh - the day shift manager basically made dough in a huge (!!!) Hobart all day long, then measured out fistfulls for the different sizes. Nothing was brought in frozen like larger pizza chains. The day drivers would usually help cut up the veggies, etc.
- We made buckets and buckets of ranch at a time - several huge containers of mayo, pour in a few half gallons of buttermilk, and mix together with the ranch powder mix. We would then use a beer pitcher to dip into the huge plastic bucket, then pour into the small plastic containers that eventually get thrown into the pizza box.
- The Tuesday roll special started right before I graduated and left CS. To me, non-Tuesday rolls tasted better than Tuesday rolls. To meet the insane demand, the day shift manager and driver would make 100s and 100s of rolls throughout the day. The rolls would stay in the cooler until needed - and I think that little bit of prepared down time takes away from the freshness. But any Gumby roll is better than a Double Dave's roll.
- During rare down times - we made a small crowd in the 'box room' just standing their folding pizza boxes, one after the other, until there were several columns of multiple sizes nearly to the ceiling.
- Some people slacked, others, like me, hustled (because I was a broke college student). It was a great job that you could make decent money at if you didn't mind the craziness, the hours, etc.
- I bet I still have a Gumby's shirt somewhere...
So many other crazy stories - lots of us were big partiers - that probably shouldn't be discussed in a public forum.

Edit to add Double Dave's...