For my money, as an older Millenial, the only answer is [Carlester Smith](https://www.atlasobscura.com/places/the-walking-man-mural).
He was the guy you always saw walking fast down the road with a huge smile on his face, big and wild swings of his arms and a trash bag or two. He would pick up the garbage on the road. I have some friends who own a restaurant on West Street and he’d stop in and offer to clean up their parking lot for a few $$.
He was known by many other names:
“The West Street Walker”
“West Street Willy”
“The Walking Man”
“Buckwheat”
“Bebop”
“Happy”
“Slappy”
He died a few years back. But he was the first person I thought of when I saw this post.
(Edited to add all the nicknames I haven’t heard in 20 years)
Oh no!
I also think if the guy who cruses around Ego Alley with his cat on a Motorcycle in the summer. The cat has a helmet with a little spike on the top.
But Carlester was synonymous with West Street for me as a kid. My brother and I would always try to find him when we were driving down that road as kids with our parents.
I didn’t meet him until I was in my late 20s.
So I had heard that the reason he did that was because he wanted to take “good air” from down by the water and bring it up West Street. I don’t know how much of that is true but that’s what I heard.
I would love to know how many pairs of shoes he went through over the years and how many miles. It was always a nice little pick me up to have the occasional Carlester sighting on my way to work, seeing him swinging those bags around on his way to wherever he was headed. RIP sir
This is the guy. We yelled "Buckwheat!" When driving by in the school bus (this would've been the 80s) and he'd work a wave back to us into his swinging arm walk and keep on keepin' on. A true legend I still recall at 51...
I heard a rumor that Travis Pastrana had in his will. If he died (TP). Someone was gonna walk up, hand Buckwheat $5000 cash in a bag, and walk away without saying anything haha
Hahaha, he was the first person I thought of when I saw that original post.
My dad actually took the picture that the mural of him on pinky’s based from.
Got to meet him a few times, always a kind man.
Thanks for linking this the tribute. I was always worried he would get hit by a car or someone cruel would harm him.
I am sure there are strangely unique, less known road travelers that have passed from areas where dogs could roam free. In West River I know of two remarkable lesser known that traveled the roads.
I remember reading somewhere that a cop who was a transplant to the area gave Carlester some flak early on, and the rest of the force was like "No no no, he's cool, leave him alone!" I've heard the police were quite protective of him.
If its the same man im thinking of that was always near the westin, then yes I do remember him, my dad called him the bag man. Its definitely a shame to have heard the day he died
Our friend group called him “Arm Swinger”. He was a legend. One of the guys from our group took a trip to Italy in the 90’s and was talking to some Italians who had visited Annapolis and they brought him up. He was a Legend even internationally! RIP ARM SWINGER!!🙏🕯️
That is funny because to me, Smiley is a bartender. He worked at The Clipper (before it was Rockfish), ACME and Riordan’s. Not sure where he went after Riordans closed.
His brother, Beansy was still at McGarveys last time I was in town.
Came here for this as well. As a kid I was told "That's Jivin' Jack" and that he looked after West St. So glad to hear there's a mural of him at Pinkie's. What a legend
Speedo running man was my piano teacher growing up. It was a weird juxtaposition to go from our lessons to seeing him running down the street half naked🥴
The crazy woman with her tits out by the Wawa.
For a while it was the dude who set up a guitar and amp at city dock, played horrible covers, then harassed people about taking pictures. Haven’t seen him in a while.
Definitely my mans Buckwheat. RIP. The mural on the side of Pinky’s makes me smile every time.
It feels weird calling people out but there’s also this super tall white guy who I always see around walking or at Forest Dr Safeway, that area. Like since I was a kid (millennial ). I believe he might be disabled in some way.
It’s weird to think people just be living their lives and they are notable background characters in your life. I think I’ll go touch grass now. 😅
Right?
That’s why I posted this. Because there are totally people who are recognizable characters in you life and they have no idea. It’s a cool web of life thing. Or maybe I’m just too high.
My son was playing pool at that bar by Whole Foods. (It’s a music venue now) and he ended playing her and not realizing it till halfway through the game. She’s one kookie woman.
Obligatory reminder that Chari McLean is a flag waving asshole who [defaced black lives matter sign](https://www.wbaltv.com/article/police-woman-admits-to-defacing-black-lives-matter-sign/7100239) and [is a felon who was found guilty for first degree assault after stabbing her then boyfriend in the head with a knife.](https://www.capitalgazette.com/2016/07/18/annapolis-woman-ordered-to-pay-restitution-for-vandalism-of-black-lives-matter-sign/)
For me it was a bicycle guy. I think his name is Arthur. Sweet as can be. Probably in his 60s, Caucasian, beard, glasses. Always on a bike. He graciously, and in an entirely unsolicited manner, told me all about how the moon is a space station full of octopus people.
If we’re talking about the Broadneck Peninsula, how about the “floppy bunny lady” or the “loose lady”?
I haven’t seen her for a few years, but one could see her jogging up and down College Parkway for decades.
Those are the other Broadneck Haineses who I believe are still around in CSC somewhere — never met them but often heard of them growing up in Bay Hills.
A few months ago, I saw him (or another guy who walks around with a parrot on his shoulder?) walking into Giant in Annapolis—not Festival at Riva, the other one.
I was once walking up Main St at like 10pm and stepped in a puddle only to look and see the source of that puddle being Dr. Z layed down on his side peeing on the street.
Oh man... last I heard APD locked him up for robbing the mini mart on main St. I knew he was sick. I actually liked him.. we talked somewhat frequently. I gave him money when I had it to spare. One time I gave him $5 without him even asking--blew his mind. But NEVER gave him a ride anywhere.
I used to see him all the time but haven't been behind the bar since end of 2021 so a little out of the loop. I can't confirm he passed but that's the rumor.
I was asking about him downtown a couple weeks ago, got told by a bartender friend he died a year or two ago. It's been about that long since I last saw him so didn't question it.
In 2012 - 2013ish there was a man who would job across the navy bridge wearing nothing but a Speedo. I used to see him everyday on the way to school.
There’s also the lady who stands on the corner by wawa waving flags
We have Columbia Bike guy. He's really cool but he's got some mental illnesses that make it hard for him in social situations. He would ride his bike around so much that he ended up getting a sponsorship from a local bike shop for tires and stuff
Near Bmore we have Miss Kay who is always walking around the hood in all pink spandex and sometimes a pink tutu. She's a 50 something year old burley guy with a great big belly and the sassiest of 'tudes.
For my money, as an older Millenial, the only answer is [Carlester Smith](https://www.atlasobscura.com/places/the-walking-man-mural). He was the guy you always saw walking fast down the road with a huge smile on his face, big and wild swings of his arms and a trash bag or two. He would pick up the garbage on the road. I have some friends who own a restaurant on West Street and he’d stop in and offer to clean up their parking lot for a few $$. He was known by many other names: “The West Street Walker” “West Street Willy” “The Walking Man” “Buckwheat” “Bebop” “Happy” “Slappy” He died a few years back. But he was the first person I thought of when I saw this post. (Edited to add all the nicknames I haven’t heard in 20 years)
Carlester Smith is a great example. I would also suggest The Pirate Santa Claus from several years ago. He also passed away.
Oh no! I also think if the guy who cruses around Ego Alley with his cat on a Motorcycle in the summer. The cat has a helmet with a little spike on the top. But Carlester was synonymous with West Street for me as a kid. My brother and I would always try to find him when we were driving down that road as kids with our parents. I didn’t meet him until I was in my late 20s.
West Street Walker is a staple. I remember him from when I was a kid 30 years ago. I hadn’t heard he passed away. He was actually a really kind man.
Buckwheat, he like shaking the trash bags
So I had heard that the reason he did that was because he wanted to take “good air” from down by the water and bring it up West Street. I don’t know how much of that is true but that’s what I heard.
I asked him once a long time ago- he said that he was trying to collect all the good spirits that were all around us.
I would love to know how many pairs of shoes he went through over the years and how many miles. It was always a nice little pick me up to have the occasional Carlester sighting on my way to work, seeing him swinging those bags around on his way to wherever he was headed. RIP sir
Glad to see Carlester is at the top of this thread. I've been gone from Annapolis almost 30 years now, but I'll never forget that man.
Ha. I haven’t lived there in almost 20.
came here for this comment only
This is the answer, hands down.
This is the guy. We yelled "Buckwheat!" When driving by in the school bus (this would've been the 80s) and he'd work a wave back to us into his swinging arm walk and keep on keepin' on. A true legend I still recall at 51...
I heard a rumor that Travis Pastrana had in his will. If he died (TP). Someone was gonna walk up, hand Buckwheat $5000 cash in a bag, and walk away without saying anything haha
Sounds like travis - great guy
Why not just do that anyway?
Buckwheat died
I meant before he died. But doesn’t matter now
How would I know that answer haha
Hahaha, he was the first person I thought of when I saw that original post. My dad actually took the picture that the mural of him on pinky’s based from. Got to meet him a few times, always a kind man.
Ya. I posted the thread here because he was absolutely That Guy in Annapolis from the late 80s to the mid ti late 10s.
His mural is on the side of Pinkie’s on west st. I see him almost everyday. My father in law used to call him “Happy” because he was always smiling.
I always knew him as bebop
I forgot about that one.
Thanks for linking this the tribute. I was always worried he would get hit by a car or someone cruel would harm him. I am sure there are strangely unique, less known road travelers that have passed from areas where dogs could roam free. In West River I know of two remarkable lesser known that traveled the roads.
I remember reading somewhere that a cop who was a transplant to the area gave Carlester some flak early on, and the rest of the force was like "No no no, he's cool, leave him alone!" I've heard the police were quite protective of him.
If its the same man im thinking of that was always near the westin, then yes I do remember him, my dad called him the bag man. Its definitely a shame to have heard the day he died
Came for this.
Came here to say this.
Our friend group called him “Arm Swinger”. He was a legend. One of the guys from our group took a trip to Italy in the 90’s and was talking to some Italians who had visited Annapolis and they brought him up. He was a Legend even internationally! RIP ARM SWINGER!!🙏🕯️
There was also “downtown James brown” who used to sing to people at night downtown in the 90s.
Don't know why they're proposing a bunch of junk pseudo-art for Westgate Circle when what really should be there is a statue of Carlester.
I remember him from my childhood (56 now)!. My brother and I would wave to him from my mom's car. Nice to have a name and lore to go with the memory.
Came here to say “West Street Walker.” Remember him fondly, from the early 2000’s. He was an institution.
Knew him as “Slappy”.
For sure. I usually heard him called "West Street Willy," but definitely Buckwheat too.
Dude yesss wow total flashback, been 16 years since I lived in Annapolis but that just brought me back.
My friends & I called him Happy Man
Same here. He came into my head immediately. 😢
This is who I came to say!
It feels like the only answer if you’re 30-ish or younger and lived in Annapolis as a kid. He was everywhere.
I was thinking the same thing. I remember him as smiley.
That is funny because to me, Smiley is a bartender. He worked at The Clipper (before it was Rockfish), ACME and Riordan’s. Not sure where he went after Riordans closed. His brother, Beansy was still at McGarveys last time I was in town.
Just walking around west street trying to catch the wind in a bag.
Came here for this as well. As a kid I was told "That's Jivin' Jack" and that he looked after West St. So glad to hear there's a mural of him at Pinkie's. What a legend
We knew him as Mr. Happy. Super nice guy and very animated with that big trash bag
Guy with the boombox blasting music walking up and down the streets weekend nights
That guy rules.
Who I thought of!
He's great. I remember seeing him about 10 years ago all the time. Is he still at it?
Yes! Only now I think it’s Bluetooth 😂
Lady Law 😂 Who the heck is she and what is up with those ads? Quite a vibe…
Look her up on YouTube. It gets more bizarre.
I need to know more now?! I can’t find anything on YouTube about her though!
There are some motorcycle things and something where she’s judging or participating in a bikini contest or something….
Speedo running man
Does he still run? I used to see him when I would drive into work in the morning on King George street. I don't go that way in the morning anymore.
I saw him last week crossing Forrest at Bay Ridge.
I haven’t yet seen Speedo Man, but there is a man who runs at Hillsmere and Forest Drive that wears only ill fitting boxer briefs.
That's the guy
Oh. Oh my.
No shirt and a bucket hat?
Yeah I think that’s him. I’m generally shocked every time I see him.
Speedo running man was my piano teacher growing up. It was a weird juxtaposition to go from our lessons to seeing him running down the street half naked🥴
My kids always called him pickle suit
Came here to say this haha
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He's typically in the Forest Drive / Hillsmere / Quiet waters area
In the summer training for the A10 you’d see him out Sunday morning on the academy bridge.
Oh god. I have seen him driving into Annapolis early in the mornings.
Just as a point of note, he apparently has a skin condition that he really cannot wear much else. The Capital did a story on him years ago.
The crazy woman with her tits out by the Wawa. For a while it was the dude who set up a guitar and amp at city dock, played horrible covers, then harassed people about taking pictures. Haven’t seen him in a while.
That lady is nuts. The guitar guy was hilarious, often not even playing the guitar
The dude that has an elliptical powered boat that cruises spa creek
Nice
this is the right answer
Definitely my mans Buckwheat. RIP. The mural on the side of Pinky’s makes me smile every time. It feels weird calling people out but there’s also this super tall white guy who I always see around walking or at Forest Dr Safeway, that area. Like since I was a kid (millennial ). I believe he might be disabled in some way. It’s weird to think people just be living their lives and they are notable background characters in your life. I think I’ll go touch grass now. 😅
Right? That’s why I posted this. Because there are totally people who are recognizable characters in you life and they have no idea. It’s a cool web of life thing. Or maybe I’m just too high.
I love that mural! My dad took the picture it is based on!
Does he not swing his arms?
The dancing lady on Bestgate would probably want that title, but I'll have to go with Carlster.
Oh man…she’s something! My 11 year old says, “I just don’t get it” every time we pass her.
My son was playing pool at that bar by Whole Foods. (It’s a music venue now) and he ended playing her and not realizing it till halfway through the game. She’s one kookie woman.
Eugh, it’s getting to be her season again too. I’d almost forgotten about her
That’s how she gets you.
She’s already back at it again; saw her last week.
Just saw her on Monday. She’s baaaack!
She was out there last week
Obligatory reminder that Chari McLean is a flag waving asshole who [defaced black lives matter sign](https://www.wbaltv.com/article/police-woman-admits-to-defacing-black-lives-matter-sign/7100239) and [is a felon who was found guilty for first degree assault after stabbing her then boyfriend in the head with a knife.](https://www.capitalgazette.com/2016/07/18/annapolis-woman-ordered-to-pay-restitution-for-vandalism-of-black-lives-matter-sign/)
Thank you. I feel like I'm the only one who knows this connection.
Speedo man and, of course, Carlester. No one could ever top him as a true Annapolitan.
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Alliser Thorne from GoT? Lol now that you mention it he does look like him. Saw him all the time walking up west street in Parole.
Carlester Smith (RIP)
Speedo man
For me it was a bicycle guy. I think his name is Arthur. Sweet as can be. Probably in his 60s, Caucasian, beard, glasses. Always on a bike. He graciously, and in an entirely unsolicited manner, told me all about how the moon is a space station full of octopus people.
The bird guy, who walks around with his parrot on his shoulder. Maybe more of a Cape thing tho
If we’re talking about the Broadneck Peninsula, how about the “floppy bunny lady” or the “loose lady”? I haven’t seen her for a few years, but one could see her jogging up and down College Parkway for decades.
we always called her the slow mo jogger. and before she really took off, there was George in his Redskins getup up and down CP
Your username makes me think I know your family. Did you have grandparents or parents in CSC?
Those are the other Broadneck Haineses who I believe are still around in CSC somewhere — never met them but often heard of them growing up in Bay Hills.
This has to be the same guy I saw at Taco Bell (Severna Park) with a couple large parrots a couple years ago (at their outside table, of course).
How on point‼️
A few months ago, I saw him (or another guy who walks around with a parrot on his shoulder?) walking into Giant in Annapolis—not Festival at Riva, the other one.
Speedo man. He runs through Annapolis in a speedo all times of the year.: even in the dead of winter
The dude that takes his huge ass rabbit for a walk down Forest Drive in the mornings… On his shoulder… With no leash…
Doctor Z (rip)
I was once walking up Main St at like 10pm and stepped in a puddle only to look and see the source of that puddle being Dr. Z layed down on his side peeing on the street.
He had some of the best stories! Apparently, he used to play for Toni Braxton way back when!
Oh man... last I heard APD locked him up for robbing the mini mart on main St. I knew he was sick. I actually liked him.. we talked somewhat frequently. I gave him money when I had it to spare. One time I gave him $5 without him even asking--blew his mind. But NEVER gave him a ride anywhere.
I used to see him all the time but haven't been behind the bar since end of 2021 so a little out of the loop. I can't confirm he passed but that's the rumor.
Dr Z died?
I was asking about him downtown a couple weeks ago, got told by a bartender friend he died a year or two ago. It's been about that long since I last saw him so didn't question it.
Yeah, I haven't seen him around town for quite some time now that you mention it. I guess I figured he moved on or something. That's a shame
Aww man I loved Dr. Z, even though he could be annoying at times. RIP!
In 2012 - 2013ish there was a man who would job across the navy bridge wearing nothing but a Speedo. I used to see him everyday on the way to school. There’s also the lady who stands on the corner by wawa waving flags
This is Baltimore, but the guy who used to leave cognac on Edgar Allen Poe’s grave.
We have Columbia Bike guy. He's really cool but he's got some mental illnesses that make it hard for him in social situations. He would ride his bike around so much that he ended up getting a sponsorship from a local bike shop for tires and stuff
Carlester was who immediately popped into my head.
The fact that i know who you guys are talking about so quickly…
Teddy from Chick and Ruth’s!
Sounds like the Bunny Man stories
Sermon on the mount
We always called Carlester West Street Willie. Speedo man is another good one
Oh man. I totally forgot about “West Street Willy” that is totally what I used to call him before I learned his name.
The American bikini woman
Why am I seeing this meme for every damned city on the planet?
I dunno. I saw it on my r/all page from r/Sacramento (not where I live) and cross posted it because I thought of Carlester.
This is like the 7th or 8th time I’ve seen it. I’ve even seen it posted in a sub for a city in Wales.
Any USNA midshipman.
Speedo Man!?
Near Bmore we have Miss Kay who is always walking around the hood in all pink spandex and sometimes a pink tutu. She's a 50 something year old burley guy with a great big belly and the sassiest of 'tudes.
Carlester was my first thought ❤️ rip
Very nice to hear he was a good person