“Tip on quite a few bucks?”

Sampras rival during the 1990s

Get on board

Let off steam, perhaps

Perry Como or Bing Crosby

Frustrated and making poor decisions, informally

#1 on Wired magazine's list of the 10 most influential video games of the 2010s

"Aren't we all hoity-toity?!"

Generate clippings, say

First name in hog riding