Many people in this thread are confused by Drake wearing his underwear while swimming, while I know people who go into the pool with their underwear on.
Do you wear underwear in the pool? If not, do you find it odd that people swim with their underwear underneath their swim trunks?
No. If your swimming trunks chafe you/can't contain your junk, buy a pair from Target instead of Walmart. It's not hard to buy nice swimming trunks in 2015.