Selfish Mom

Why Do I Give Money To Funny Homeless People?

Aug 3, 2008 What's Going On

I don’t give money to people on the street that often. I used to. Pretty much every time I saw someone begging, I’d give a dollar or two. It seemed like the nice thing to do. Made me feel like I was doing something without actually going to too much trouble. But then I moved to the New York City area ten years ago, and I had to stop. I would have gone broke. I would occasionally buy food for someone, or give them a dollar in a weak moment. But it became the exception rather than the rule.

One thing that consistently has me getting out my wallet, though, is humor. I remember one man who appeared out of the shadows of some scaffolding and said “Hey lady, care to make a donation to the United Negro Pizza Fund?” It was six in the morning, and I was late for work and in a huge rush, but this man managed to make me laugh. How could I not give him money?

There was one guy I came across in Times Square. He was tall, blond, and didn’t look too dirty. More like a backpacker who hadn’t taken a shower in a few days than a homeless person. He had a sign that said “Six foot tall white Jewish guy will rap for $2.” I didn’t give him any money. I didn’t have to: he had a crowd around him and was making cash.

The first couple of times I saw someone with a sign reading “Who am I kidding? I need to buy more beer” I gave some money. But now those signs are so ubiquitous that I hardly notice them anymore.

Last week, I passed by this man on Chambers Street.

I chuckled, but kept walking. Something drew me back, though, so after about two blocks I turned around.

I approached him and crouched down on the sidewalk in front of him. He saw immediately that I was holding a five dollar bill and something in his face woke up. I introduced myself and gave him the five dollars – I didn’t want him to think that I was trying to buy his attention. He could have the money even if he said no to my question. I asked him if I could take a picture of him for my blog (it didn’t occur to me at the time that he might have no idea what a blog was, but I’m sometimes myopic that way) and he said yes.

I felt pretty stupid taking a picture of him, so I did it as quickly as I could. I felt like some tourist, who would later rattle off the places she had visited during her trip to New York City. “I saw the Chrysler Building, and FAO Schwartz, and met a real live homeless person!” So I snapped one picture and then moved closer and sat down across from him.

I asked him if he’s found that humorous signs garner more money than other signs. “Absolutely. Cynical humor works.” He calls himself the Sidewalk Cynic. Has he ever tried sincere, pleading signs? “Nope, didn’t even try.”

So I asked him what some of his other signs have been. The only two he could think of on the spot were “Brad and Angelina are having twins, and I need money for a gift” (very funny) and “Nicole Kidman won’t date me – I don’t have enough money” (not as funny, but he gets points for trying).

I had to get home and was already on the verge of being very late, so I couldn’t stay any longer. I gave him a half smile and said, “If I want to contact you again, there’s no way for me to do that, is there?” He smiled back and said “Sidewalk Cynic at Yahoo.” We both laughed. I wasn’t ready to give him my number. Funny as he was, he was still begging for money on the street for reasons I hadn’t had time to ask him.

So, why do I tend to give money to people who make me laugh? It hardly seems fair. Surely other homeless people are just as hungry or need their fix just as much. I’ve been trying to figure it out since I met Sidewalk Cynic. I think it’s because humor makes them seem more human, as opposed to some drunk, incoherent guy asking for change so that he can buy some liquor and get even more incoherent.

When I see someone who has managed to hold on to his humor despite what he’s going through, I know that he’s held on to some part of his former self, and it gives me hope that he could reverse his fortunes. It shows intelligence. Sidewalk Cynic is obviously keeping up on at least some current events, he hasn’t completely removed himself from society. And instead of playing on the sympathies of passersby, he’s betting that humor will grab people’s attention, and he’s proven himself right. I hope that someday he gets to put his skills to better use than begging. But until that day comes, I’m glad he’s found a little bit of success for himself with his humor. And I’ve got a five in my purse for him just in case I see him again.

Originally posted on Selfish Mom

Tags: Brad and Angelina, chambers, Hillary Clinton, homeless, Manhattan, New York City, Nicole Kidman, NYC, Sidewalk Cynic