Hi. I'm an experienced DNDer from days of old, but I'm new to 5e. I'm just creating my first character, and I already have a question. I'm an artist in real life, and so my question, not surprisingly, is about the Performance skill. The description for this skill indicates it applies to all forms of expression. Choose the appropriate form for the situation and roll the dice. Got it. Now, in choosing the Entertainer background, you're asked to choose 1-3 'routines'; your specialties, I assume. My question is... For situations in which a Performance roll is called for, and if your character possesses the Entertainer background, might a small bonus (+1) be appropriate when performing one of your chosen routines? And similarly, might a small bonus (+1) also be appropriate when a separate skill may benefit from your additional experience with these routines? For example, as an Entertainer, I choose Actor and Tumbler as my routines. At some point in my adventures, I need to make a Deception roll, and after that an Acrobatics roll. Might my experience with these routines provide a small (+1) bonus to those rolls? It seems reasonable to me that a character who makes his/her living performing, and practices certain routines more than other routines, would be somewhat more likely to perform successfully than another character who does not make a living in this way. Your thoughts?

That will be up to your DM. 
Generally, this edition doesn’t use situational bonuses or synergy bonuses. If you’re coming from 3e, for example, you’ll find the math in 5e is a lot tighter, so that +\-1 matters more.

Instead, there’s advantage/disadvantage. Where you roll 2 d20’s and use the higher (advantage) or lower (disadvantage) roll. That’s what I’d be more likely to give you if I were DM.

Rules As Written: No. But, as always, the DM has the final say in the matter. 

Generally, if you have two proficiencies that apply to the same check, you get advantage on the roll. (Optional rule from Xanathar's, iirc.) Thus, if you wanted to paint an artistic mural, and you had proficiency in Performance and Painter's Supplies, then you would have advantage on the Painter's Supplies check. 

In your Deception then Acrobatics example, you're already making two rolls. So you probably wouldn't get anything extra. Maybe advantage on the Acrobatics if you rolled really high on the Deception. 

One of 5E's shortcomings is how poorly written its rules for skill and tool proficiencies are.

5e as written uses Proficiency to represent what you've described. So as an Entertainer, you gain Proficiency in Acrobatics and Performance; those Proficiencies represent your practice at those crafts from your background. By default, that's all the bonus you get; you're not automatically any better at those skills than someone who has proficiency from another source, like the Bard or Monk class. If you want Expertise (which doubles your proficiency bonus) in those skills, there's a Feat for that, or you can get it from the Bard, Ranger (Tasha's Cauldron of Everything version only), or Rogue class.

Your DM might choose to grant you advantage on a check that aligns particularly closely something from your background, but that's completely their prerogative. You can ask, but be ready to hear "no".

Quote from GrayHero >>

Hi. I'm an experienced DNDer from days of old, but I'm new to 5e. I'm just creating my first character, and I already have a question. I'm an artist in real life, and so my question, not surprisingly, is about the Performance skill. The description for this skill indicates it applies to all forms of expression.

Quote from Rathkryn >>

Thus, if you wanted to paint an artistic mural, and you had proficiency in Performance and Painter's Supplies, then you would have advantage on the Painter's Supplies check. 

It's worth noting that by RAW Performance does not seem to cover "all forms of expression"; the description of the skill from the PHB/Basic Rules reads "Your Charisma (Performance) check determines how well you can delight an audience with music, dance, acting, storytelling, or some other form of entertainment.", indicating that it's intended towards the classic acts you would carry out in front of an audience. Generally speaking, a proficiency bonus for creating something comes from having the right tool prof, such as the Painter's Supplies mentioned above, but imo you're really stretching RAW to say you should get advantage for having a Performance prof as well.

Quote from The_Ace_of_Rogues >>

 

It's worth noting that by RAW Performance does not seem to cover "all forms of expression"; the description of the skill from the PHB/Basic Rules reads "Your Charisma (Performance) check determines how well you can delight an audience with music, dance, acting, storytelling, or some other form of entertainment.", indicating that it's intended towards the classic acts you would carry out in front of an audience. Generally speaking, a proficiency bonus for creating something comes from having the right tool prof, such as the Painter's Supplies mentioned above, but imo you're really stretching RAW to say you should get advantage for having a Performance prof as well.

I think this distinction is important.  Performance is not "execute in all media".  I could see a DM arbitrate the scenario using the artisanal tools of an "artists paints" (as opposed to say a barn painter etc) and maybe use the performance for the artists role is "entertaining interpreter" of their art.  That is it's a tool check to accomplish the painting, then "performance" would be used to almost as way to persuade audiences to accept the vision, or curation, or arrangement of canvases etc.  .... getting into major Warhol territory.

As it is, D&D breaks down as a simulation game when it comes to artistic production (and probably linked in that way to the crafting in general rules lack).  Fudging and granting is often what's used in DMing artists.

Thanks for all the replies! So, if I'm reading this correctly, artistic skill and Performance are separate? In this case, possessing tool use in a lute, for example, lets you play a piece of music competently, but without any special effect on the listener(s), whereas Performance with tool use allows the performer to please the audience such that they may be willing to show their appreciation of that performance via good will, gold, favors or affections? That does make sense, now that I think about it, and gives characters with the Entertainer background the extra advantage of having a few of those skills to start with (i.e. their routines). And if a character without the Entertainer background (i.e. no routines and/or no applicable tool use) possesses the Performance skill, then what? A bard is obviously competent with several musical instruments and lyrical techniques, but without the Performance skill, his mundane performances are academic only?

If by allows, you mean allows you to try, then you’re on the right track. 
In general, as in earlier editions, you describe what you’re trying to do, then your DM will determine if a roll is appropriate. If there is no chance for success, for example, they may not even tell you to bother with the roll. No matter how good your song is, the king is not going to give you his country, that kind of thing. 
But if you’re just trying to put on a show. Then usually the DM will call for a performance check, and see how good of a show you put on. Your proficiency in a given instrument may not be a factor, as someone above said, tool proficiencies are really not well defined. But I’d suggest mentioning your proficiency in the lute when doing your performance; the DM may then choose to give you advantage or some other kind of bonus.

One of the big things in this edition is they’ve gotten away from the 3e style of trying to have a rule for every situation. The idea is broad guidelines and allowing the DM to make rulings in each situation.

There’s also a section in Xanathar’s Guide to Everything with rules for earning money long term under the work part of the downtime section. It comes down to make a roll for the week and see how good of a lifestyle you can earn for yourself. 

Instruments and Performance are a really fuzzy grey area. And there is not nearly as much RAW divide between specific sorts of actions like you're describing. Painting is separate from Performance because it's very much not indicated by the name, and as a rule of thumb any kind of crafting/production of something is covered by tools rather than skills, and isn't really all that supported in 5e because it's not much of a simulation game.

I generally divide it with Performance being things you do in front of an audience that don't involve an instrument, such as singing, dancing, pantomime, or storytelling.  Anything that's a form of crafting, like painting and sculptures, is a tool check- the only time that Performance could come into play is if you're trying to paint in a way that entertains an audience.  Where things really get fuzzy is when you try to combine playing an instrument with singing or dancing at the same time.