Bard Character Concept

[Allistar]

How would you build a version of a classic jazz singer like Dean Martin, or Frank Sinatra? I just had the idea to make a bard and since those are the kind of artists I'm obsessing over right now I thought it would be fun to try and make something like them in D&D. What college do you think he'd go in? I'm genuinely interested to see where this goes!

[Tawmis]

College of Glamour, I'd say.

Because both are charming and charismatic... So one thing I think that fits is: Enthralling Performance
https://rpgbot.net/dnd5/characters/classes/bard/

Mantle of Inspiration: Reposition your entire party and grant temporary hit points. You won't need to use this in every fight, but certainly don't hesitate to use it if you think it will be helpful.
Enthralling Performance: Similar to Charm Person with a 1-minute casting time, during which you need to somehow hold that target(s)'s attention and during which you can't be interrupted. Charm Person is a 1st-level spell and it will have the same DC, and creatures don't know that you attempted to affect them with a spell unless the spell explicitly says that they do, or if there is some visual effect (like a ball of fire).
Mantle of Majesty: There are a number of spells which charm a creature, including charm person. By charming a creature and using command to prevent the creature from using their turn (Drop and Grovel are great options), you can mostly paralyze a creature. Unfortunately, since you don't use a spell slot command is cast at its minimum spell level and will only affect one creature. This will work great to lock down strong single enemies, but in a fight against a group you probably don't want to use this.
Unbreakable Majesty: This is an amazing option both defensively and offensively. Make sure to buff your AC or look for other defensive options so that you won't get killed, but you should strongly consider drawing attacks specifically to force this effect on enemies. Disadvantage on saving throws against your spells in the following round means that a well-chosen save-or-suck spell can immediately take the creature out of the fight.

[Chrizzt]

You don't have to be a bard to be a fine performer.

For Frank Sinatra (who allegedly has connections to the Mafia) I more envision some kind of rogue, perhaps with Expertise in Performance.

Edit: I'm sorry, I missed the point where you explicitly said you want to make a bard.

[Allistar]

You don't have to be a bard to be a fine performer.

For Frank Sinatra (who allegedly has connections to the Mafia) I more envision some kind of rogue, perhaps with Expertise in Performance.

Maybe he's got the criminal background and the feature of "criminal contacts" is something like the mob.

Also, yeah I was thinking bards. Although your idea has just sparked another in my head. That of a silver tounged rogue that melts hearts with persuasion and performance alike.

[zinycor]

Well, things like the build are secondary to the personality and charm you should bring to the group. Personally, I would try doing Frank's voice and try sliding into song whenever possible.

I had lots of fun playing an Elvis Presley character. Good luck.

[Man_Over_Game]

College of Glamour, I'd say.

Because both are charming and charismatic... So one thing I think that fits is: Enthralling Performance
https://rpgbot.net/dnd5/characters/classes/bard/

Mantle of Inspiration: Reposition your entire party and grant temporary hit points. You won't need to use this in every fight, but certainly don't hesitate to use it if you think it will be helpful.
Enthralling Performance: Similar to Charm Person with a 1-minute casting time, during which you need to somehow hold that target(s)'s attention and during which you can't be interrupted. Charm Person is a 1st-level spell and it will have the same DC, and creatures don't know that you attempted to affect them with a spell unless the spell explicitly says that they do, or if there is some visual effect (like a ball of fire).
Mantle of Majesty: There are a number of spells which charm a creature, including charm person. By charming a creature and using command to prevent the creature from using their turn (Drop and Grovel are great options), you can mostly paralyze a creature. Unfortunately, since you don't use a spell slot command is cast at its minimum spell level and will only affect one creature. This will work great to lock down strong single enemies, but in a fight against a group you probably don't want to use this.
Unbreakable Majesty: This is an amazing option both defensively and offensively. Make sure to buff your AC or look for other defensive options so that you won't get killed, but you should strongly consider drawing attacks specifically to force this effect on enemies. Disadvantage on saving throws against your spells in the following round means that a well-chosen save-or-suck spell can immediately take the creature out of the fight.

This has my vote, too. Any other Bard is going to be focused on things other than being charming and charismatic, but the Glamour Bard is the only one who only does that.