Why for the life of me I can’t stay awake when listening to Music?

First, you've got great speakers, and your system is likely very good.

Second, since you're still working, the issue is not likely that you're getting too much sleep, which research is showing can be detrimental to major organs. Eight hours/night is a good target for older folks.

Third, the suggestions to get a health check-up (once a year) and examine your lifestyle and activity level are very sound advice. Working from home can be very lethargic. Even just taking a walk around the block after lunch can be helpful. Hitting a gym 3 times a week would be fantastic. You'd be surprised how many older dudes are doing this to improve their quality of life.

Fourth, have your doctor check your PSA level. It's a simple blood test for prostate cancer. It's the second leading cause of cancer death among men, after lung cancer. Early detection can greatly improve survival rates.

Fifth, turn the volume up to concert level.  

Many people have suggested great things that I’ll affirm with a personal story and add one more. I was so tired when I moved to Cali for work that I would sleep 12 hours a day and could barely function. I first went to an allergist who said I had no allergies. I then went to an GP who was an Internist, Hemotologist, and an Oncologist. My mom passed from Leukemia so I thought I may have that. He sent me to an allergist that he knew (also doubting I had allergies) and when they tested me I blew up like a balloon (I wasn’t stuffed up like normal people but my tongue was swelling). First issue found. I went to the doctor for some time getting blood tests and my iron and platelets were really really low, probably leukemia. He had me change my diet and ran tests weekly. I got a bone marrow biopsy and after it was all said and done I don’t have cancer. I have an extremely rare blood disorder where my platelets are 10 times larger than normal so I have fewer of them. He then said I needed to take a multivitamin and a small iron pill because my body wasn’t absorbing iron from food. I did that for a few days and with the allergy medicine I felt great! All that from those two simple things. (Most other doctors would have been having me go through a bone marrow transplant, I’m so lucky I had a really good doctor). Edit (The rare blood disease is May Hegglin’s Anomaly and I am normal, it doesn’t affect me in any way.)

Lastly get tested for sleep apnea, that was my latest life changing find. I wasn’t breathing while sleeping for 30 seconds out of every minute out of 58 minutes in an hour. Basically I was gasping for air as a reflex not to die and never truely sleeping. I would fall asleep immediately when I got home from work and sat in a chair. I couldn’t make it through a few songs much less a TV show. When you a machine, get the nose pillow, you don’t need a chin strap the positive air pressure keeps your mouth closed (this was 1000 times better than any mask I tried) I swear I wake up feeling like I’m superhuman because I’m actually sleeping. I have dreams again and I am enjoying life so much more. My last checkup the Dr said that as many as 60% of Americans could benefit from a CPAP machine. I am an extreme case and now the biggest advocate. 
 

FYI You would never guess I had any of these things seeing me, I’m athletic and physically fit, don’t have high blood pressure, etc. I did not match the profile for any of this stuff. 
 

Good Luck and I hope my story inspires some people to get looked at.
 

- Steve

The same thing happens to me.  It really doen't matter on the music style.  Usually I dose off for a few songs.  I think it's because my mental mood changes and I release the stress and relax.  After a few songs I come back and then just continue my listening.  I don't mind because I feel really good after a quick cat nap.

+1 @hifidream recommendation to get tested for sleep apnea.  Getting a CPAP machine has been life changing.  I wish I had done it sooner.   I use a full mask as the nose pillow didn't work for me.

I still like to nap while listening to music.