James,
Dents may be a little too sharp for this but suggest you leave car in sun to get hot then apply dry ice to the dents to see if the metal will return to normal shape. Walmart or similar store normally carries the dry ice. It it doesn't work, it won't do additional damage.
 

James, Adding to Bill's idea above which is worth a try, two decades ago I owned a '51 Commodore 4 door with a series of nearly identical dents. The car didn't have a headliner which allowed access for several hours of gentle and persistent hammer and dolly work. A skim coat of polyester filler across the entire roof surface followed by block sanding (80 grit) made it flat and smooth. High build primer followed by more sanding (240 grit then 400 grit) and finally paint made it look better than new. This is not a difficult job but does take time and elbow grease. Hint --from start to finish expect this job to take 10 to 20 hours depending on skill/experience, tools, and degree of perfection sought. Material cost will land between $150 to $450 depending on skill/experience and shiny pigment quality used. Hope this helps.

As one who has done this before and has been doing paint and body work for years (since the 70's), I would be shocked to see this job done properly take less then 35 hours total. The last one I did was a 52 Wasp roof that looked like a tap dancing class had been held on it. It is now is laser straight with the roof curve. It has a 3 stage paint job that is show quality.
The head liner needs to be removed in order to work the dents out from underneath. It is best to have someone up top that can lightly tap the dent perimeter ring down while one is pushing up. Get them as close as you can. When these dents were made it also stretched the metal. That "stretch" needs to be dealt with, I use a shrinking disc and a wet cloth, the disc heats the area up and the wet cloth shrinks the heated metal as it cools down. (I quit using a torch after I tried the shrinking disc).
I do that multiple times in order to achieve the look and feel I want and to get it ready for a coat of epoxy primer, don't flood it on, you only need coverage, then apply a very light skim coat of quality filler.
Once to that point, I skim it and when ready, use a long board that has some flex (working on a big curved roof) and using 36 grit, block that off. It is important to use a long board, not the little short sanding block, this allows the work area to be spread and helps prevent highs and lows. Deal with any high spots and then skim and work out again until I am happy with the flat/curve. I use 80grit for the second blocking.
I then spray with a high build blocking product such as PPG K38 urethane primer or Quick Sand blocking primer. Begin another series of blocking using finer grade paper, I go to 120 or 180 depending on the primer, and graduate up to 320 DA or 400 hand block.
There are a lot of tutorials out there that explain the process.
https://garage.eastwood.com/eastwood-chatter/block-sanding/
your results will vary depending on experience and materials.

Kerry, I have to laugh. When I first wrote my post I actually wrote the job would take 25 to 30 hours but then thought to myself, "That's due to your OCD, most "normal" people can probably get it done in half the time." So I reduced my estimated hours. Well now I'm happy to read your post. But I'm also a tiny bit worried this might mean you also might suffer from the same OCD! LOL 

Great post with lots details on the materials --thank you.             

I don’t have near as much experience doing body work as Kerry, but I’ve done my fair share. I don’t see any way to repair that without removing the headliner. That could be good news, if you we’re planning to replace it anyway. Otherwise, it’s a PITA. And a pain in the neck, since you have to work over your head in a tight space.  

Let me suggest that you first take it to one of your local “paintless dent removal” experts, and ask what they can do for you.  I’m sure you will still have to remove the headliner, but I’ve seen them work out dents like that back to original contours with no repainting and no filler.  Since your paint is already damaged, you will have to repaint, but you may spare yourself many hours of bodywork if they can straighten the metal for you.  

I decided to teach myself body work on my '51 Pacemaker after it got hit on the left side.  The roof was one of the biggest challenges.  I got it as flat as I could manage with hammer and dolly but managed to raise a welt in one spot that wouldn't go back down - it looked like a pimple.  I decided that if I couldn't lower the welt, I'd raise the rest of the roof to its level, 1 coat of high build primer at a time, sanding between coats (about 5 hours per coat).  I can report that this worked and the roof looked really good...150 hours later!!  Yes, I have 30 coats of primer up there, and it's held up remarkably well in the New Mexican sun, even 3-4 years later.  Of course, the car got hit and totalled last year, so the whole right side is now trashed...but the roof still looks nice!

Time in = results out, so far as I've heard and experienced.  

Oh, one other thing - a club member out here (who has sadly since passed) told me every Hudson roof is dented, and it's all his fault.  You see, when he was a kid, he and his friends played this game where they'd climb up the front bumper of step downs, walk up the hoods, walk across the roof and slide down the backs.  And that's the origin of your (and my) dents!

[quote="Robert Waid post=28039 userid=12727"]Kerry, I have to laugh. When I first wrote my post I actually wrote the job would take 25 to 30 hours but then thought to myself, "That's due to your OCD, most "normal" people can probably get it done in half the time." So I reduced my estimated hours. Well now I'm happy to read your post. But I'm also a tiny bit worried this might mean you also might suffer from the same OCD! LOL 

Great post with lots details on the materials --thank you.             
 
              Robert, Yes I have some of that as well. Par for the course if one is going to do body and paint for showing. I guess that is the reason I have so hard
a time with the "rat rods" we see today. I do understand why people do it, due to the cost of material and time involved in trying to achieve "perfection".  I took an "auto body" class in Tech school when I was in High School. It wound up being a worthless class due to the teacher being more interested in our attendance than teaching.  All the things (and I mean everything) I supposedly learned in that class, I had to learn to unlearn if I wanted to do the job right.
I learned my trade by constantly reading and getting my hands on material that would help me learn and then applying it until I was satisfied I knew what I was doing.  One thing I have learned, you never learn it all!
 I went to forums like "Auto Geek" to learn new methods of color sanding, buffing and polishing my paint jobs. A world of difference since I began! Primers, paint and related materials are very different today than they were 40 years ago!
A few years ago I decided to buy a totaled Honda Ridgeline to rebuild as I wanted to see how it would be compared to the older vehicles I had worked on. When reading the official Honda repair manuals, I was actually shocked to find out that every Honda dealer body shop I checked with did not rebuild to the Honda specs (I was looking for a source for the special welding wire that is required to properly weld the new high strength steel that new cars are now built with)
When finished, my Ridgeline went thru the state inspection with flying colors, but I don't know if that is saying much as I feel it was such a poor inspection process. I would be leery about buying a "rebuilt total" from anyone else.
 

Discard

[quote="John Morningstar post=28069 userid=5970"]I decided to teach myself body work on my '51 Pacemaker after it got hit on the left side.  The roof was one of the biggest challenges.  I got it as flat as I could manage with hammer and dolly but managed to raise a welt in one spot that wouldn't go back down - it looked like a pimple.  I decided that if I couldn't lower the welt, I'd raise the rest of the roof to its level, 1 coat of high build primer at a time, sanding between coats (about 5 hours per coat).  I can report that this worked and the roof looked really good...150 hours later!!  Yes, I have 30 coats of primer up there, and it's held up remarkably well in the New Mexican sun, even 3-4 years later.  Of course, the car got hit and totalled last year, so the whole right side is now trashed...but the roof still looks nice!

Time in = results out, so far as I've heard and experienced.  

Oh, one other thing - a club member out here (who has sadly since passed) told me every Hudson roof is dented, and it's all his fault.  You see, when he was a kid, he and his friends played this game where they'd climb up the front bumper of step downs, walk up the hoods, walk across the roof and slide down the backs.  And that's the origin of your (and my) dents!
               That "pimple" was caused by metal being stretched. It needed to be shrunk to get it back to level.  I used to do that using a torch and wet rag, I now use a shrinking disc and wet rag.

You are 100% correct, and I tried heating the spot with a torch, but I either used too much or too little heat and couldn't get it to shrink. After repeated efforts I did manage to make the metal thin and brittle (and the bump worse) which is when I decided to raise the rest of the roof to match. Not a recommended technique, but I really botched it and didn't know how else to fix it. As the saying goes, "Experience is the thing you get right after you needed it." The only silver lining of that car getting totalled was that I had already butchered the roof, although my cover-up still looks pretty good, and the multiple coats of primer are hanging in despite my hot climate.

Greatly appreciate the responses.  I tried one place and they were afraid they would just pull the paint off, which is exactly what happened when I tried with a kit I bought. Headliner is not bad so I was holding off on that but I understand it is probably necessary to do it.   At least I have a project for the summer.     Thanks   

James, if I remember right, the steel in Hudson stepdowns is 19ga. It is much less in modern cars so the glue/dent pullers work much easier. When I pull dents like yours, I use a stud welder dent puller and hammer tap the dent "bulge" around it to even things out.
https://www.amazon.com/Motor-Guard-JO1500-Magna-Spot-Professional/dp/B0000AXDA6/ref=sr_1_4?dchild=1&keywords=spot+welder+dent+puller&qid=1623713686&refinements=p_89%3AMotor+Guard&rnid=2528832011&s=automotive&sr=1-4
But you will almost always have some shrinking to do especially on a large surface like a roof.
https://www.youtube.com/watch?v=IGuc06GMwG4

That's quite an improvement on how I did it "back in the day" with drilled holes and screw in slide hammer.
thanks for the info.