Slightly younger stars Musiq Soulchild and Anthony Hamilton both proved easy crowd pleasers too, mixing slow jams and swaggering hits, and both with their silky voices in fine form.
Mos Def and his two DJs had no trouble rousing the crowd for the more hip hop motivated section of the evening, with his verses throughout fitting snugly in the pocket of his many varied beats.
Hip Hop, Undeniable, Mathematics, and Umi Says stood out, and the suave performer left the audience with a few sage thoughts as he finished with a prayer.
Common proved to be a highlight of the evening, elevating the party atmosphere as the sun slowly descended. He started with the distinctive Forever Begins, kicked it up a notch with Go!, and slid his way into a mash up version of You Don't Know My Name with his impressive female backing singer taking the Alicia Keys part.
Come Close got the ladies swooning, and his two DJs injected a good dose of nostalgia with snatches of House of Pain and Michael Jackson blended into the set.
Classic favourite The Light, and brand new track Kingdom proved to be highlights, and it seemed like Common was on a roll, but he was running half an hour over schedule, so his music was cut.
He wasn't pleased, and it left the crowd momentarily perplexed, but kudos to the organisers for trying to keep things running loosely to schedule.
Soon enough D'Angelo was ready - with an eight piece band to boot.
He performed the first song from behind the piano, offering a fairly jammy introduction to his set, but quickly moved out front for Left & Right, and Really Love.
The set seemed a little too mellow at first, for a crowd primed to party at 9pm, but by the time he hit the hits - One Mo' Gin, My Lady, and How Does This Feel - he'd made it feel like a very special night indeed.
The man might not have the same six-pack that he used to, but his piano playing and voice were in top form, and his band ridiculously tight.
The same could be said for Maxwell, looking very smooth in a white suit as he strutted on stage to a remix of Ain't No Sunshine.
His six piece band, including horn section, were there to bring the groove, which is precisely what they did with Sumthin' Sumthin', Get to Know Ya (complete with some saucy gyrations from Maxwell), Everwanting (with an excellent super tight bass intro), Bad Habits, and yes, he played his famed cover of Kate Bush's This Woman's Work.
You could almost hear the sigh of satisfaction from the crowd.
If it'd been a couple of degrees warmer, with a touch more sunshine, it would've been a perfect festival. As it was the party atmosphere and excellent performances rose above the dark clouds, and made it a day to remember. Let's hope SoulFest is back next year.
What: SoulFest
Where: Western Springs Stadium
When: Sunday October 26, 2014.