Jackie Robinson West is playing in its first Little League World Series game, and Common can’t stop sneaking peeks at the TV in his Trump Tower hotel suite. The South Side–raised rapper and actor is supposed to be discussing the themes of inner-city Chicago violence and hopelessness that run through his critically praised new album, Nobody’s Smiling. But 13-year-old Pierce Jones keeps hitting home runs.

“That’s my friend’s nephew!” Common says excitedly when first baseman Trey Hondras comes up to bat.

An official Jackie Robinson West hat, with “42” stitched on the front, sits atop the bureau in his suite’s bedroom. The cap, a gift from a friend who is close with the team, is a little too big for Common. But he’s not the baseball-hat-wearing type anyway. Head shaved and sporting a thin goatee (and, today, an abstract designer T-shirt from Wicker Park’s RSVP Gallery), he’s always been more partial to newsboy caps or—in his more beatnik Erykah Badu–dating days—knit kufis.

The team from Chicago is on its way to an easy 12–2 win, so Common turns his attention back to the subject at hand. “In the poorest parts, in the ghetto, when I was growing up, there still was some hope,” he says, leaning in. (He was raised in Calumet Heights but now lives in Beverly Hills.) “And you go a generation before that—my mother didn’t have a lot of money, but she could sleep with her door open. There was just a certain code and culture and integrity and a type of respect for self that just existed. Right now, the situation has become so bad, and you know, I’m not an economist, but they say there’s no middle class anymore. It’s the poor and the rich, and there’s so many poor people that have lost hope.”

Spend any time listening to him talk, and it’s easy to see how Common earned the tag “conscious rapper” coming up in the gangsta-rap-dominated ’90s. He went his own way, rhyming about topics like spirituality and love. Today, at 42, he’s proved himself a rare commodity in hip-hop: a still-relevant elder statesman.

“When you’re in your 20s, you think you know a lot,” he says. “And when you’re in your 30s, you’re like, ‘I don’t know too much.’ And then for my 40s, it’s been, ‘Who gives a fuck what I know?’ You don’t have as much to prove.”

You have to go back to 2005’s Be, produced by his friend Kanye West and nominated for four Grammys, for the last Common album to make a significant impact. But of course, the guy’s been busy doing other things, like, you know, pursuing acting (he stars in AMC’s Hell on Wheels, a western now in its fourth season), writing a best-selling memoir (2011’s One Day It’ll All Make Sense), and dating Serena Williams (they’re no longer together; he’s currently single).

Nobody’s Smiling, which came out in July, may not break any sales records, but it’s the most urgent, angriest music Common has made in a while. On the first song, “The Neighborhood,” he raps: Crack babies / Momma’s a push / We were the products of Bush. On the title track, he declares: In the Chi, ain’t a damn thing funny.

“I have the enthusiasm again for making music,” he says. “For some years, I don’t think I had it.”

He put two of the city’s up-and-coming rappers—Lil Herb, 18, and Dreezy, 20—on the album to bring attention to young artists. His foundation, Common Ground, is organizing Aahh! Fest in West Town’s Union Park this fall with the same goal, along with another: to train young people in jobs related to putting on such events. “They’re gonna be able to learn different aspects of production and music, where it’s not just like, ‘I gotta be the rapper.’ ”

As for the music coming out of this city these days, Common is politic. He argues that even the most violence-filled Chicago rap is infused with a certain soulfulness. “Guys like Chief Keef can only speak from their experience. He’s telling the story in the way he can.”

Common’s own experience was similar, but it differed in important ways. Born Lonnie Rashid Lynn (family and friends still call him Rashid or, simply, Rash), he was raised in what he described in his memoir as “a black middle-class neighborhood rubbing up against poverty. You had hardworking families with plenty of kids, but then you had gangbangers, too.”

His father, Lonnie, a onetime DuSable High School basketball star who played a season in the red-white-and-blue-ball ABA before drugs derailed his career, was a loving, if sporadic, presence in his life. Common’s mother, Mahalia Ann Hines, raised him while working in marketing for Liquid Paper and Gillette and running three daycare centers she owned. Hines, who still lives in Chicago, would go on to become a public school teacher and eventually a principal, one with a doctorate in education.

“I believe God gave me a gift, but the things that helped me nurture that gift were implanted early,” Common says of his mother’s influence. “Poverty of love causes so much violence. When you truly got love, and you know you got love, it helps you function better, you feel better about yourself, you care more about other people, you care about the neighborhood you’re from.”

Just as Common starts to get deep again, Monard “Moe” Lee, one of his childhood friends, arrives to lighten the conversation considerably. Moe, a burly guy wearing a Lacoste shirt with an outsize crocodile, brings up the impromptu freestyle rap battles he and Common had as teens driving around in Common’s Hyundai. Needless to say, it was never a fair fight.

“Moe was my freestyle beat-up dummy,” Common says.

“Yeah, I was the victim,” Moe laughs.

Moe is now a real-estate agent.

Moe is here to accompany Common to a South Side barbershop for a video shoot for the remix of a Lil Herb song called “Fight or Flight.” Common lent a verse to it. The rapper slips on a gray hoodie, and he, Moe, and two assistants file out of the suite and into a waiting car. We’re not even five minutes into the drive, heading along Ohio toward Lake Shore, when Common exclaims, “Hey, that’s Lupe!”

Sure enough, there’s rapper Lupe Fiasco, chilling outside CRC Music & Post, the famous studio where everybody from Michael Jackson to Nine Inch Nails has recorded. We don’t stop—we’re running late—and Lupe recedes into the distance. Suddenly Chicago feels both grand and intimate.

We arrive at 88th and Stony Island, not far from where Common grew up. Josephine’s Barber Shop is smaller than the Trump suite yet filled with more people. Common, it turns out, has been here before; his stepfather used to take him for haircuts as a child.

Most of the people are just onlookers (friends, assistants, a couple of older guys actually getting haircuts) jammed against the wall and by the door. Sitting in a barber chair, Common raps his lines as he gets his (already bald) head shaved.

The low-budget shoot is missing the craft services and Teamsters that Common has grown accustomed to since moving to Los Angeles in 2005 to pursue acting. He had several small roles in big films (American Gangster, Date Night) and starred in one (Just Wright, opposite Queen Latifah and playing an NBA star) before becoming a central character on Hell on Wheels. Still, he listens intently to 22-year-old director Danielle Alston and follows her outside to shoot a scene.

Common and Lil Herb are an odd couple. Lil Herb, whose real name is Herbert Wright, is shorter and less demonstrative than Common. But mostly, he’s just a lot younger. In fact, he’s only a year older than Omoye, Common’s daughter with an old girlfriend, and was four years from being born when Common’s debut album, Can I Borrow a Dollar?, came out in 1992. (At that time, Common went by Common Sense.) “I grew up a big fan,” Lil Herb says of Common. “He’s a real lyricist, an artist who tells a story. He comes from the same struggle as me. We relate.”

As the shoot winds down, a small crowd lingers outside Josephine’s, most with cell phones out. Three middle-aged women run over from a beauty salon next door. “Hey, just right! You look just right!” one of them yells, playing off the movie title and jumping up and down.

After 20 minutes of photos and hand-shakes and 10 more minutes inside a Harold’s Chicken Shack (just fries for Common, a pescetarian), his two assistants manage to get him into an Uber SUV that’s taking him to the South Shore Cultural Center. He’s heading there for a quick rehearsal of a motivational talk he’s giving the next day to teens as part of the Nike-sponsored World Basketball Festival.

Common spends the first half of the rehearsal turning the first verse of “The Neighborhood” into a spoken-word piece. The second half he hashes out a conversation he’ll have with the moderator on the event’s central theme: what it takes for young people to “rise up.”

As we get back on Lake Shore Drive, a brief report comes on the radio about a late-afternoon rally at Daley Plaza to protest the police shooting in Ferguson, Missouri.

“Damn, we should have gone,” Common says to everybody and nobody. (Ten days later, at the MTV Video Music Awards, he will initiate a moment of silence for the teenager who was killed.)

We have one stop left: CRC Music & Post, where Lupe Fiasco—wearing long dreads, large round sunglasses, and baggy camo fatigues—has spent the day recording a remix of his song for the fundraising initiative Stand Up to Cancer. Also on hand is Jennifer Hudson, who’s singing the chorus. She has her young son with her.

Lupe wants Common to contribute a verse. An engineer plays the song while Common closes his eyes and bobs his head. Lupe’s lyrics are the opposite of standard saccharine charity-song fare. “Fuck cancer,” he raps furiously. “If I die, it dies with me.”

Common asks what he can add to a song that already sounds complete, and Lupe tells him to replace the second verse. For a moment, Common, respected above all else for his lyricism, looks a little nervous.

Later, as Common and Hudson chat, I ask Lupe, who is 10 years younger than Common, about the rapper’s influence on him. He begins by trying to remember the opening lines to the 1997 Common song “Invocation”: Envisioning the hereafter / Listening to Steve Wonder / On a quest for love / Like the “Proceed” drummer.

“That dude right there is the king of lyrics in Chicago, him and Twista,” Lupe says. “He was an integral part of me discovering rap. It’s rare to get, like, an ahh moment repeatedly in the same song, or in the same verse, and he’s one of the dudes who can still do it.”

Common’s plan had been to go back to the Trump to watch a Bears preseason game, a rare chance to relax with his Chicago friends. But now he says he’ll forgo the game to hole up in the suite’s bedroom and work on his verse for the Lupe song.

Maybe he does still have something to prove.