You could name almost any Police or Talking Heads hit.
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I am the lead singer, front man and music director of 3 projects while playing bass. So I call the keys, assert the tempos, hand off solos, listen to everybody in the band and fill the gaps, all the while reading the audience and planning the next songs 2 or 3 ahead of where we are. What makes me able to do that is when a play I have to have my part down so darn cold it can operate on auto pilot. So when we learn new stuff I put in lots of "gym time" prepping for the new song rehearsal by drilling until I can play the song with my eyes closed and not referencing the frets. I don't cut corners on rhythm and put in 3 hours of rehearsal prep on my own for every 1 hour of band rehearsal. It works for me and because of that commitment I can attract great players into my projects. But I haven't met many players as willing to work that hard. But there are still tough songs to vocally phrase correctly while laying down a professional quality bass line!Alright, singing bassists. What are/were the most challenging songs for you to sing while playing?
Did you give up on any?
If not, how did you master them?
Rule #1....
Divorce your mouth from your hands. I find that if I learn the bass line like the back of my hand, I can simply "let go" of that aspect of concentration and let the muscle memory take over with my playing. I am then free to have fun with my vocals, and my vocals performance improves.
"Mama I am depending on you to tell me the truth" - That's a tough line to nail…I would think.Papa was a Rollin' Stone
Call me Al (Paul Simon) has been the toughest so far that I had to do.

Beginnings by Chicago is one that I think I'm playing OK while singing and then realize I'm not in time with anyone else. Or, I can just play it and not sing it and everything's fine. So, when that song comes up, I'll pickup an Electric/Acoustic or just swap instruments with the guitar player and I'll play guitar and sing it because playing guitar and singing it is a no-brainer. I've done that for many, many years.Alright, singing bassists. What are/were the most challenging songs for you to sing while playing?
Did you give up on any?
If not, how did you master them?