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There’s a reason I keep coming back to see Mac DeMarco: his shows are incredibly fun.

This was my fourth time seeing the Canadian singer-songwriter, and every set I’m reminded that the prodigiously talented don’t have to be so self-important to be good. From afternoon sets at music festivals sponsored by salad companies to a massive club – with a few raucous small shows in between – I’ve deeply enjoyed both the music and the performance on every occasion. Wednesday night DeMarco and his band played a long, winding set that lasted slightly over two hours and included a surprise second encore to an audience of several thousand.  It was silly and kind of bro-ey and certainly goofy, but deeply charming.

Surprisingly, The Anthem originally felt a little big for DeMarco and his band, as the venue was only about half full at the time the show got underway. Part of it was heightened expectations due to the fact that he sold out the 9:30 Club on two consecutive nights last year; the more subdued song selection to kick off proceedings didn’t help either. But the audience loosened up and seemingly doubled in size within the hour (maybe the teenagers were outside Juuling?), and soon it was a classic Mac DeMarco show rife with crowd surfing, sing-alongs, and slinky slacker rock. And while they perform under DeMarco’s name, each member of the band has his own cult-like following and rapport with the audience: there were loud yelps and screams of approval any time guitarist Andy White carved out a solo, bassist Jon Lent laid down a groove, or keyboard player Alec Meen played a motif in between songs. Despite the rotating cast of musicians who have floated in and out of DeMarco’s orbit in recent years, it very much maintains the sense that this is a “band”, even if the Edmonton native is the sole songwriter.

Speaking of songwriting: as DeMarco has grown up, so has his work. That’s not to say that mature themes are new to his music – songs such as “Chamber of Reflection” and “Still Together” revealed flashes of a thoughtful, considerate artist years ago – but now there’s a more nuanced understanding of mortality, love, and forgiveness throughout his recordings. Arguably this is welcome depth from someone who self-describes his style as “jizz jazz”, but don’t worry – there’s still no sign of self-importance or pretension to be found anywhere: they remain a bunch of fun-loving goofballs and weirdos.

It’s been about a year since DeMarco put out a record, 2017’s This Old Dog, and the band’s comfort with the material means they’re taking interesting liberties with the live versions of songs. There’s an underlying ease to band’s stage presence and it translates to slower, stretched out renditions of the hits that pay close tribute to their roots in psychedelic rock. These new arrangements demonstrate the band’s depth of talent in addition to their underlying delight in fucking with people. Throughout the night there was always the sense that they were all in on some joke that flew over the majority of the (very young) audience’s head – echoes of Jonathan Richman meets Jens Lekman bubbled up often – but it was all infallibly polite and awkwardly funny.

DeMarco clearly loves making and performing music, and it’s most apparent in how he engages with fans. Sets are generally loose, and although they’re not quite as casual as taking requests from the audience, it’s not terribly far from that in reality: the band is happy to play fan favorites, and quick dialogue between them on stage in response to an audience shoutout can lead to a shift in the next song to play at the drop of a hat. This is most apparent when doing the usual cover or two; normally we’d get a minute long snippet of some mid 90s track with drummer Joe McMurray on vocals. However Wednesday night we were treated to a whole forty minutes of off-key crooning by McMurray as DeMarco sat on the drums. And although it sounds unappealing, try telling that to the crowd hollering along to every word of RHCP’s “Under the Bridge”,  Weezer’s “The Sweater Song”, Radiohead’s “High and Dry”, and “Kiss Me” by Sixpence None The Richer. It was a glorious mess, and had me grinning ear to ear. As the house lights went up at The Anthem, the crowd kept baying for one more song, and a few minutes later they had their reward. DeMarco came back to the stage accompanied by Meen on keys, and patrons who were halfway down the Wharf scrambled back to the floor. Commanding them all to sit down cross-legged, DeMarco serenaded us all with a moving song about his strained relationship with his father. It was a surprisingly, and appropriately, heartfelt ending to the evening.