Conor Oberst has matured a great deal during his two decades in music.

Conor Oberst, 34, has been making records for most of his life. Over the past two decades, the Bright Eyes mastermind has released more than 20 full-length albums. You can practically listen to him grow up on record. This weekend, Oberst performs at the 9:30 Club with backing band (and opening act) Dawes, supporting his latest solo record, the folksy “Upside Down Mountain.” How’d he get there? We’ll explain.

1998 ‘If Winter Ends’ (From Bright Eyes’ ‘Letting Off the Happiness’)

The blistering song finds an 18-year-old Oberst making suicide threats while literally screaming “for the sunlight” as he equates his teenage depression to a never-ending winter, begging for spring to melt his frozen heart. It’s one of his rawest emo moments and a stark contrast to his present persona.

2002 ‘Let’s Not S— Ourselves (To Love and To Be Loved)’ (From Bright Eyes’ ‘Lifted or The Story Is in the Soil, Keep Your Ear to the Ground’)

This 10-minute tirade marks Oberst’s initial foray into ’70s-minded political rock. The rollicking song bursts with horns, crunchy guitar solos and a yelping Oberst condemning “cowboy presidents,” the education system, the media and war. With a dose of angst and pointed opinions, the song bridges the gap between his emo tendencies and more mature, Dylan-esque folk-rock. The times they were a-changin’, indeed.

2005 ‘We Are Nowhere And It’s Now’ (From Bright Eyes’ ‘I’m Wide Awake, It’s Morning’)

In 2005, Oberst released an electro-pop album and a country-folk record on the same day. The latter, “I’m Wide Awake, It’s Morning,” dove headfirst into twangy singer-songwriter territory with its uncharacteristically warm and relatable country ballads. With Emmylou Harris on backup vocals, this gorgeous folk song finds Oberst surveying an existential limbo while drifting asleep in the passenger seat of a directionless car. He plays Gram Parsons pretty well, especially for an ex-emo kid.

 2014 ‘You Are Your Mother’s Child’ (From Oberst’s ‘Upside Down Mountain’)

One of Oberst’s most poignant songs to date chronicles a boy’s childhood through the eyes of his aging father. It’s a simplistic acoustic folk song as heartwarming as it is tragic, culminating in the father’s recognition that the son will be a better dad than he ever was. Though previous songs touch on similar topics, Oberst has never sounded so in love with life, or so balanced. There’s no angst or aesthetic dissonance, just admiration for life’s unrelenting ebbs and flows.

9:30 Club, 815 V St. NW; Fri., 8 p.m., $35 & Sat., 8 p.m., sold out; 202-265-0930. (U Street)