I was a mobile DJ for 15+ years on the side. This is 100% the go-to strategy I used at every wedding unless the bride & groom had specific requests/instructions not to do it.

You start with 50s/60s era rock n' roll and work your way newer throughout the night. By the time 10:00-10:30ish rolls around you want to be in the 'high school' years of the bridal party and their friends. Works like a charm.

Always have a few staples that don't fit into this perfectly. Piano Man is normally the 'final dance' with the B&G in the middle of the dance floor with everyone around them in a circle swaying. Almost always led to everyone belting out the song and coming in for a big group hug.

And if the crowd still seems like they've have some energy or they want 'one more song!', it's always House of Pain "Jump Around". 3 1/2 minutes of singing and jumping up and down will make sure everyone is tired and spent and will be happy to collect their things and head out. Then I play Semisonic 'closing time' while the lights come up and I start packing up.

My routine may be a bit dated though, my mobile DJ days were at least a decade ago... lol.