I’d pick his favorite song if he had one. My dad LOVED the old Mac Davis ditty Hard to be Humble. But if you’re looking for a theme try one of these:

God Bless the USA
Wind Beneath My Wings
Thanks for the Memories
My Way
Sittin’ on the Dock of the Bay
Easy Street
Bang on the Drum All Day
40 Hour Week
Blue Skies
Changes In Latitudes, Changes In Attitudes
I’m Free
You’ve Got a Friend

Have them sing this song:

My Dad was a Navy WWII Vet - not sure of this is approprate for you Dad’s retirement buy I think it’s kind of neat:

Sailor, rest your oar
Sailor, rest your oar
When your final dive is made, and your battery’s running low,
You’ll know there lies a boat for you many fathoms here below,
With your annunciators jammed on full and your depth guage needles bent,
Your accumulator’s dry of oil and your air banks all are spent,
It’s then you get to wonderin’, is my life’s boat rigged for dive?
Your guessing drill commences, am i dead or still alive?
You pace the flooded decks with scorn and curse the flaws of man.
Into realms of rex you’ve stepped, and here you’ll make your stand.
To live your life, as sailors must, at the bottom of the sea.
There’s one you’ll have to reckon-that one, my friend, is thee.
Will your conscience do you justice when the final muster’s in?
Did you lead the kind of life you should in every port you’ve been?
The answers to these questions and many, many more,
Are locked in the hearts of sailormen from cannes to singapore.
So, when your day for mast rolls ’round. the choice is up to you,
Sailor chart your course of life right now. chart it straight and true.
Now’s the time to flood your tanks and trim up ‘fore and aft.
It’s a trifle late when the klaxon sounds to square away your craft.
Your final billet lies below, on old ocean’s floor.
So, be ready when that last word’s passed.

Sailor, rest your oar!

Whenever we come back from a deployment, they play the song God Bless the USA from Lee Greenwood. Brings a tear to my eye everytime!!

I don’t know if it’s appropriate for a retirement but I do know it’s appropriate for any service member

I Will Always Love You

Why not pick a song your father loves to hear you sing? This is his day. I am not convinced you need to select a song that relates to the military, but more importantly, relates to what your father enjoys hearing from you and your sister. What a nice tribute, by the way. God bless! And thank your father for his duty to our country.

take this job and shove it?
just kidding
THANK YOUR DAD FOR HIS SERVICE
and now Im drawing a blank
theres a country song out about 4 years ago that is patriotic and good. I cant think of the name though sorry
maybe someone else can name it for me

Some male family member making a speech/toast would be way more appropriate for the occasion. Singing will seem tacky.

When I’m 64