Another view in somewhat of an essay on the topic...
I look at this a bit differently. First off, most of what we play is either standards (Route 66, Almost Like Being In Love, Orange Colored Sky and so forth) or what most would call "slightly stale pop", tunes that were current some ten or more years ago (Love Shack, R&B/funk stuff from the 1970's, and so forth). Much of this would not be considered appropriate as an "opener" of the type that is there to grab your attention.
However, different sets at different times during the evening require a different approach.
For what I call the "cocktail set", the first of a typical evening, we always ease in with music that does not stifle conversation. Other than our most recent event (where I allowed the organizer to program the tunes - big mistake), I would usually use something like Cute, this to let people know that there is music but not to blow their heads off. The first set gets a lot of low intensity, classic pop tunes but few vocals.
For the second ("dinner music") set, I tend to plug in a standard from the Fifties or Sixties - something by Mancini, or some recognizable yet innocuous movie theme music (Theme from Picnic/Moonglow, or something like that). Once again, it's intended to let them know we are playing, but to remain below the general level of conversation as the guests enjoy their dinner.
(I even have a couple of medley style arrangements of "Dinner Music" that (together) will fill an incredible ten minutes of time. The guys hate them, as they are "old" music and require a lot of doubling on flugelhorn and clarinets, but they do the job just fine. Besides, how often do you get to play There's A Small Hotel these days?)
Towards the end of the second set (after the dessert has been served), I like to start plugging in what I call "performance numbers". These are tunes that the vocalist do very well, but are more like "sit and listen" stuff rather than dance stuff. I do a mean Misty on baritone, off of the Basie fluty arrangement, we have tunes from shows and movies that fit well here (Somewhere Over The Rainbow, Someone To Watch Over Me and so forth. In effect, it's a bit louder, but not so much so as the dance sets.
For the third, fourth and fifth sets ("the dance sets"), I like to open with something that builds up to the first "non-opener" tune in the set. In effect, it serves to rap at the door, announce that things have changed, and that now it's time to dance.
For a set that starts with R&B, I use a rearranged version of Dick Spencer's instrumental version of I Can't Turn You Loose (aka, "The Blues Brothers opener"), followed immediately (with nothing more than a four beat count off) by I Feel Good. From that point out, I block groups of three and keep the four-beat dance stuff flowing for the rest of the set.
James Brown and Tina Turner are good role models here. But, you have to have the vocalists to carry it off. I once did, and now (after a hard two years rebuilding) I have so again.
(For a less R&B oriented crowd, I might use something like Almost Like Being In Love or our upbeat version (non-Bobby Darin) version of Blue Skies. They are only commercially available tunes, but both really brighten things up after ten minutes of interval music. Another winner is And All That Jazz, which I have dreams of pairing with the overture from Chicago as soon as I get it transposed into the correct key. I also have the Barnett arrangement of Sidewalks Of New York (aka, "East Side, West Side") on the way from Lush Life Music that will serve this purpose as well.)
Stuff like Jump, Jive & Wail!, or Zoot Suit Riot would get plugged in at the end of this set, as it's a good way to keep the energy flowing into the break.
For the final set, it may be R&B or it may be country, dependent on the crowd. However, I always trend towards four beat music, as few bother to learn swing dancing or waltzing any longer.
Now, what about closers?
This is where I tend to stick the flashy, more "performance-oriented" numbers. Last Friday, we used Big Time as one of these (although misplaced by the client), and it is a rousing success in that role. I generally use the Les Brown arrangement of Sweet Georgia Brown as a middle of the night closer, thus allowing the guys who have put up with fifty minutes of boring pop to cut loose on a jazz chart for a change. (It's also a good test of a new lead tenor player.)
For the end of the evening, we have traditionally wound down with a lot of "slow dances", ending with a four or five tune sequence designed to showcase each vocalist at least one time. Traditionally, this runs something like Put Your Head On My Shoulder, Crazy, Georgia On My Mind, Summer Wind, followed by our theme/sign-off of Funny How Time Slips Away.
All of this is flexible, depending on who happens to be singing. Two years ago, with virtually all new vocalists (I lost my first set due to relocation, children, and artistic differences), it was pure hell to put a four set list together. Now that everyone is all rehearsed up, the opposite is true - my wife and I have to work to make sure that the best gets included, balancing out each singer's work load in two or three song clusters (the better to avoid constant switching out of the vocalists), and structuring things so that the time on stage is more or less equal. It feels really good when you know you have five hours plus of music ready to go at any one time.
By the way, my set lists have evolved a bit over time. From a straight "Number and Title" listing, the band version now lists that plus count and tempo, the vocalist expected to be singing, and a general "Notes" section that lists possible pitfalls for the first time sub and auxiliary percussion assignments.
(These are done on Microsoft Word master documents, so that all of the formatting and shading is pre-arranged. I use Word a lot, even more than Finale...)
For the vocalists, there is a separate version that has number, title, vocal assignment, "historic notes" (to give them something to structure patter with) and auxiliary percussion assignments. I have everything set up in a database, so all that I have to do is to copy a given tune from the data base and then paste it into the corresponding slot on the set list.
I program 18 tunes per fifty minute set. The calculation goes like this: 18 tunes times three minutes a tune (a good pop average figure) equals 54 minutes. (I have never had a solid fifty minutes of music in a set, however, this due to stage changes, verbal intros and outros, stage "business" and so forth.) If we were doing mostly instrumental and jazzers like Basie's stuff, that total would probably drop to fifteen.
I try to keep the inter-song gaps down to forty five seconds or less. It's hard to do this with seventeen or eighteen people shuffling through charts, but it's a goal that we now have come close to reaching.
Of the eighteen tunes programmed in a given set, three are "reserves", there in case I have to buy time with a substitution inserted on the fly. I also always program a "Reserve Set", kept at the bottom of the set stack, with another five or six "ready use" tunes in case someone has vocal troubles and I have to patch a hole.
Each set is kept in a color coded plastic folder, using the order red, yellow, green, orange, blue and clear.
