More Whimsical OEIS Sequences

For the first mentioned sequences based on fonts, what's the first number in the sequence that has less digits than the previous number?

The edit history of the “nonsense sequence” makes for painful reading.

https://oeis.org/history?seq=A133451&start=0&n=30

Can somebody explain what "less" keyword means? I'm asking for a friend.

https://xkcd.com/2016/