This is my surname. Memorize the phrase ‘Barry with an A’ and be prepared to have it be spelled wrong half the time anyway because no one listens and they just spell it however. This has even happened at new workplaces.
I lost my beloved brother Barry this year due to a tragic car accident. We miss him dearly every minute of every day. He was our bear and he fit the name in every way, he loved it! We have added a new family member and named him Bearmax, hope he's okay with that.
The name makes me think of some beer-bellied, balding guy. It also makes me think of Barry White. Two very different associations. I have a third one: it reminds me of the homoerotic song Barry by Gus Gus, or gusgus, whatever it officially is.