Ray St. Ray – Singing Cab Driver

My friend and I were going to take the 77 bus home from Diversey and Sheridan but it wasn’t coming for 15 minutes. It had some sort of reroute thing going on and it was raining so we decided to get in a cab. We were going call an über but then one turned and we found ourselves in Ray St. Ray’s singing cab.
Needless to say, it was the most interesting and entertaining cab ride of our lives. Ray sang us two songs, one about the preacher’s daughter and another one that he’d been working on recently.
We were very weirded out at first and could not look at each other without laughing but I’ve gotta say to was an enjoyable experience and so random!
We feel lucky to have experienced this! Glad she was there with me though, don’t know what it would’ve been like alone.
Keeping on singing Ray!

My husband and I looked at each other like what the hell just happened. He started singing, flicked his lights, looked back at us, swerved into the wrong lane twice and acted like that was normal. Nothing was normal here and I asked to get out blocks before our hotel. He was a rude to boot!

This guy has style for miles and what charisma! I still have to go check out his band sometime!

A gift or a white elephant. I’m still deciding.
We were astonished when after Christmakkuh dinner we hailed «The Singing Cabby.» How fortuitous and we love kitsch and music.
But there were a few hiccups.
It was Christmas evening and he didn’t sing Christmas songs. That seems like a «no brainer.» Or for that mattter sing songs related to us or our interests. You think he’d tailor them.
He criticized my friend for «clapping along off key, when said specifically not to make noise.» Lighten up, Mr. Serious. It’s a quaint custom when musicians perform jazzy stuff people clap or dance. We were feeling the tunes (and obviously tipsy) and it was Christmas so why snark? I thought musicians weren’t uptight?
The concept is interesting, but a big gamble. Like one can agree to listen but… It’s a captive audience. Like if anyone ever thought it sucked they can’t exactly tell him, or somersault out the moving vehicle.
It can go either way in positive or negative. I don’t often see people randomly doing improv or magic tricks at service jobs either. But he inspired me so much that when I was late with a report I made a dove fly out of the folder to distract my boss.

A for effort. But he’s a little snobby and c’mon…to be honest… a spaz with no talent.
And he criticized me for clapping along while he was singing. Ok pavoroti… maybe I’ll keep quiet when you preform in Carnegie hall. Until then take the praise with a little class.
Now I like street performers. As a red line guy, I’m partial to the quartet (quintet?) that sings classic r&b at jackson/​state. They are good musicians plus good performers. Thank you.
Also, a few years back there was this rapper who would freestlye for hours. Unbelievable. Commenting on what’s happening. interesting rhymes .I don’t say this lightly. the guy is probably a musical genius.
Singing cab driver on the other hand… ugh. I like napoleon dynamite as much as the next guy. but lets not pretend this is god’s gift to cab riders.
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Update…I found this link on youtube (from 2007). I only watched first minute. but if you think this is 5 stars then good for you.

best cab experience EVER. feel so lucky to have stumbled upon this guy. incredibly talented individual. If you see a nice white cab and the driver is wearing a suit, grab it, even if you don’t need the cab, you’ll never forget the experience. made my night.

If you are lucky enough to find yourself in Ray’s cab, then you are in for the best cab ride of your life. Ray is an amazing cab driver, a wonderful singer, a wealth of knowledge, an expert at witty repartee, and a snazzy dresser. He is extremely entertaining and his cab is remarkably clean and pleasant. What more could you want?

When I first got into the cab, I thought — is this really happening? Am I hallucinating from too much bourbon?
By the time I got home, I was amused, reassured, and had his song stuck in my head. He even asked if i wanted to audition for his band (they’re looking for a guitarist; I politely declined).
Your odds for finding Ray St. Ray seem to be best if you are leaving a Lincoln Square bar after 11pm on a weekend. If i remember, the cab was white and slightly cleaner than the average cab.

Wow, I must be really out of the loop because I had never heard of this guy.
I rarely take cabs, but on a random Thursday night we flagged down Ray outside the Handlebar. We were treated to him singing along to some song about French girls. Hand clapping was encouraged. All I kept thinking was «wtf?».
Yes, his singing was super entertaining. And if I had been drunk, I imagine it would have been the time of my life.
The five stars is for the clean cab and lack of «so this is how we’re going to die» that I get in a typical cab ride. I think we’re going to check out one of his shows, because I’m sure they are really a «show».

I’d heard urban legends about this guy, but in a city this large, what was the likelihood of me encountering the only singing cabbie?
It was raining, I was tired, and my aching feet would not survive another semi-​hike to the Blue Line. So I flag down the first cab I see. I get in and the first thing he says is «can I sing you a song?» Holy smokes, apparently the likelihood was better than I thought.
He provided me two songs, witty banter, and the most enjoyable cab ride I’ve ever had in life. I love living in this city.

So its St. patty’s day, and I’ve already had one of the more memorable nights ever in my life. I’m a little drunk and in Logan Square, god knows why I’m in Logan Square at this point in the night, but whatever. So in an effort to get home sooner rather than morning I hail a cab, and that my friends is when shit gets real.
So I’m politely talking to the cab driver about my night and my band that I just hung out with, when he proceeds to go into his speel about being the singing cabdriver. Ha ha, funny. It wasnt until he verbally went into the song selection menu where I figured I was either being filmed for HBO or probably on my way to being murdered in some alley… with my money being on the later, which is why i calmy yet carefully started to write his cab number and name on one of my cards and put it in my sock (so the police could find it when they examined the body). So I carefully select a song about taxi driving, can’t get any motivation for killing and raping anyone from cabdriving, right? In the end the song was cool, he was cool, and even went into banter about buildings and old Chicago. He politely and quickly got me to where I needed and I was not murdered, just given a card in rememberance of a cab ride strictly out of the twilight zone. This dude is one of the reasons why Chicago is the greatest city in the frickin’ world.

One stormy and windy night, leaving Carmela’s Taqueria after a long long evening of drinking and debauchery. Two girlfriends and I crawled into the backseat of a warm and welcoming cab… once we were on our way, our well dressed driver introduced himself as, Ray St. Ray the Singing Cab Driver!
Yeah, we were worried for about a split-second…Ray St. Ray gave us a selection of themes for the night and we happily chose a «A Cautionary Tale of Premarital Sex» as the song for our ride home. Ray rocked it!
The whole drive was strangely surreal yet totally fabulous due in part to Ray’s singing and in part to the copious amounts of vodka I had consumed. It was a perfectly surprising and random ending to the night and I hope someday soon, I will wander into the back of Ray’s cab in a drunken haze, again.

Ray drove us to a music club, and the club was kind of a let-​down after Ray’s songs. Really freaking cool.

this is literally the best cab ride ive ever had. good conversation without being awkward, entertainment that didnt make me cringe, and a nice little postcard to post in my cubicle at work.
if there were a way to request ray st. ray, hed be on speed dial.

I can’t believe other people have Unilocaled about this guy… but that’s cool actually.
Probably one of the weirdest sane person in all of Chicago. One day getting into a cab with a friend; we were arguing and that put me into a weird mood already, then out of know where the cabby said «can I sing you a song». At first I was like great this is all I need and then he said how do you feel which freaked me out a little. My friend just looked at me like what the hell do we do… run. So I told him angry, he sang a song… we clapped. Then he asked us to pick another emotion, by the time we got our destination he sang us about 4 songs and also explained who he was and what he does. He got a nice tip for improving our mood.
So if you ever get to experience this cool singer of songs, don’t run. He will make you smile

I have been lucky enough to spend lots of time in Ray St. Rays company. He is delightful each and every time you interact with him. Its always a new and entertaining expierence. Really, look him up and have him take you places– he will regale you with wonderful songs, intelligent conversation and pithy one liners.
And hes adorable.
I never thought that I would ever say that there was a cab driver that I wanted to marry, make sweet love to and have babies with, but for about 6 months last year I harbored some very dirty fantasies about Ray St. Ray!

Jenny S … Almost the same wave. Thanksgiving Day running late for dinner to a friends house and did the flag down. Jumped into a different dimension… Don’t really know if it was a cab or a reality show. The signing cab driver had ask us to pick from three topics. Couldn’t figure out which one, so he picked all three. As we fly down LSD… I began to feel like someone had slipped me a fun, but unexpected treat of some sort. It all happened so fast. Even his outfit was looking like he had picked it out to make it even more surreal. I began to giggle thinking to myself. Not, a reason for being a little late. But, how I got there. Who was this cabbie and how did we get the luck of the draw. Things have ways of happening. I will leave it at that. Ray St. Ray. I can not believe you don’t have any more reviews bud. Keep it between the lines and always keep a tune in your heart. NOTE: If you have friends in town or family and want to show them something other than the sites, Please give him a call and let him do his thing on the way to an event, game or dinner. It will be a lasting memory, fun and truly eventful. WELL WORTH THE PHONE CALL. Real fun, have him pick up your boss next time.

After having one too many after-​work happy hour drinks downtown, I felt too lazy to take the CTA home so I waved down a cab. Within seconds the cab driver began singing and made me pick a song out of a choice of five. Since I was drunk and alone and female I thought for sure that after the song I’d be strangled to death and shoved in a dumpster somewhere until finally my death is fictionalized and immortalized during an episode of Law & Order.
So to make the end a little nicer, I picked a cowboy song and sat back. Ray sang me a cowboy song and I drunkenly and nervously giggled while writing the cab number on my hand so that the police could more easily solve my murder.
But after the song he shushed me, listened to NPR and then took me home. I received Ray St. Ray’s calling card and discovered that I wasn’t just picked up by a crazy cabbie. I was picked up by a crazy cabbie with a Web site and a publicist. Maybe I was just happy not to have been killed at his hands but I left him a nice tip and rested in the knowledge that I’d made it through some weird city initiation.
He gets four stars for the singing. Would have been 5 had he not freaked me out with the semi-​crazy randomness of it.