What to do in Madison this week: Madison Comedy Week, Jazz at Five, and more Isthmus Picks

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H Warren + Sean Enfield, Monday, Aug. 7, A Room of One’s Own, 6 p.m.: H Warren, a poet and musician from Fairbanks, Alaska, examines the realities of living nonbinary in rural Alaska in their new poetry collection, Binded (Red Hen Press). Sean Enfield — an essayist, poet and short story writer who recently received an MFA from the University of Alaska-Fairbanks and whose debut collection of essays, Holy American Burnout!, is forthcoming from Split/Lip Press in December — will read from his work. Then the two will discuss their work, life in Alaska and more.

Madison Comedy Week, Aug. 6-13, various venues: From the kickoff show on Aug. 6 to a roast of Samara Suomi on Aug. 13 (both 7 p.m. at the Bur Oak), Madison Comedy Week packs in more than 25 events around the city. Headliner Mary Mack performs during a pair of free showcases closing the Sessions at McPike Park on Aug. 11-12; Comedy on State welcomes touring comics Felonious Munk (Aug. 10) and Bob the Drag Queen (Aug. 11); and you can find many more shows and ticket info at madisoncomedyweek.net.

Michelle Wildgen, Tuesday, Aug. 8, Table Wine, 6 p.m.: Michelle Wildgen, who writes beautifully about food (including, for a while, for Isthmus) is out with an absorbing new novel about women in the wine industry. Wine commerce is still very much a man’s world, and Wildgen’s protagonists must avoid various traps. Wildgen will be discussing Wine People with her Madison Writers' Studio partner, novelist Susanna Daniel. This launch party at Table Wine features wine and light snacks. Reserve an advance ticket at eventbrite.com, and read Mike Popke’s preview here.

How to Teach Grown-Ups About Pluto, Tuesday, Aug. 8, UW Space Place, 7 p.m.: Discovered by skywatchers in 1930, Pluto in more recent times was squeezed out of official planet status by the International Astronomical Union. In the 2022 book How to Teach Grown-Ups About Pluto, author Dean Regas explains the situation from the perspective of kids trying to get their adults to understand the science behind the decision. Regas, who hosts the Looking Up podcast and was a longtime co-host of the syndicated mini-show Star Gazers, will discuss the book during UW Space Place’s monthly speaker series (also available virtually on YouTube).

The National, Tuesday, Aug. 8, The Sylvee, 8 p.m.: Indie to the core, moody, atmospheric, and a little obscure, The National has been around since at least 2001 (scoring a Grammy in 2017) but in some ways has never had a higher profile than right now. The band’s latest release, this spring’s First Two Pages of Frankenstein, is a strong outing and possibly their most approachable, with more acoustic interludes and Matt Berninger’s vocals rising from drone to melody. Opening are the bright, electric New Zealand band The Beths. This is a sold-out show but who knows, you might find some last-minute tickets lurking somewhere.

Boz Scaggs, Tuesday, Aug. 8, Orpheum, 8 p.m.: Boz Scaggs and Steve Miller were classmates at UW-Madison, playing in bands together in the early 1960s. The rest is history, and both guys still tour today. Scaggs hasn’t released a new album since 2018’s blues-leaning Out of the Blues. But with a deep catalog that includes a steady stream of albums dating back to 1965 (a rare Sweden-only debut) — plus seven Top 40 singles released between 1976 and 1980, many of which are still played on the radio today — the man’s already reached legendary status. Tickets at ticketmaster.com.

Jazz at Five, Wednesdays, Aug. 9-Sept. 6, top of State Street, 4 p.m.: Jazz at Five marks 30 years of free concerts in 2023, and returns to its original home at the top of State Street for the full season. Concerts begin with a youth band at 4 p.m., except for opening night on Aug. 9, kicking off with Feestet at 5 p.m. followed by the Gerri DiMaggio World Jazz Unit. Aug. 16 features funky trio The JB3’s and a quartet led by Chicago guitarist Kenny Reichert; big band sounds are featured Aug. 23 by DB Orchestra and All That jazz; UW ensembles take the stage Aug. 30; and the season closes Sept. 6 with bands led by Madison congas/bongos master Tony Castañeda and Chicago trumpeter Victor Garcia. Find more info at jazzatfive.org.

Strobobean, Wednesday Aug. 9, Mickey’s Tavern, 10 p.m.: Cincinnati export Strobobean (Katrina Eresman, Rae Fisher and Jake Langknecht) play meandering, bass-riffy bops with off-kilter melodies that may bring to mind early songs from Throwing Muses, which is more than enough reason to make tracks to this free, 21+ show at Mickey’s. It’s the most Willy Street thing you can do today. With Madisonians Histo (whose third album, JGDC, emerged last September) and Aergo.

People Fest, Aug. 10-12, Driftless Music Gardens, Yuba: Recent rains have greened things back up in Richland County, just in time for the 15th anniversary edition of People Fest, a music and camping combo hosted by the People Brothers Band. An always-stacked lineup is extra special this year, with Saturday alone including a trio of legendary cosmic grass bands: Yonder Mountain String Band, Leftover Salmon and Railroad Earth. Along with the hosts there’s plenty of returning favorites like Gin Mill Hollow, MoonHouse and Them Coulee Boys. If you're not inclined to camp out, day passes are available; stages get rolling at 4:45 p.m. on Thursday, 10:30 a.m. on Friday and 11:15 a.m. on Saturday. Find tickets and the schedule at driftlessmusicgardens.com.

Watertown Riverfest, Aug. 10-13, Riverside Park, Watertown: If you can name the river that runs through Watertown, you get free admission to the town’s Riverfest! Kidding, the fest is free even if you think the river is the Seine. (It’s actually the Rock River, which makes thematic sense for this music-filled celebration.) Thursday night is pop night with the “Pop 2000 Tour” featuring O-Town, Ryan Cabrera, David Cook, LFO and host Chris Kirkpatrick (8 p.m.); Friday night is country night with headliners Bootjack Road (7 p.m.); Saturday is rock 'n roll, headlined by Tommy DeCarlo (8:45 p.m.); and Sunday afternoon is capped by a performance by R&B/soul pioneers The Drifters (3:30 p.m.). Fireworks follow the music Friday and Saturday, and Riverside Park will also have food, carnival rides, games, a craft fair and a lot of chainsaw art. Full schedule at watertownriverfest.com.

The Pirates of Penzance, Aug. 4-13, Bartell Theatre: With swashbuckling silliness and frothy fun throughout, The Pirates of Penzance is one of Gilbert and Sullivan’s most produced operettas. The Madison Savoyards should do well with hummable tunes like “Poor Wand’ring One” and the tongue-twisting “I Am the Very Model of a Modern Major General.” Who says the Victorians didn’t know how to have fun? Shows at 7:30 p.m. Thursday-Saturday and 3 p.m. Sunday; also, a free program for kids takes place at 1 p.m. on Aug. 6. Find tickets at madisonsavoyards.org.

Alice Cooper, Thursday, Aug. 10, Overture Hall, 8 p.m.: Yes, times have changed. Alice Cooper, glam-shock rocker of the 1970s, is playing the stately confines of Overture Hall. Why are you going to see Alice Cooper? The 2011 inductee to the Rock & Roll Hall of Fame writes anthemic songs, straddles a line between punk and goth, and yet plays straight-ahead rock ‘n roll of the kind that is in short supply these days. Plus, you can sit down. Cooper is touring in support of a new album, Road, coming on Aug. 25. Tickets at overture.org.

Our Home States, through Aug. 12, Broom Street Theater, 8 p.m.: Broom Street Theater, where local playwrights usually rule, presents the start of one of its long-term projects. Our Home States is a series of short plays that the theater solicited from each of our fabulous 50 states (though of course some are a little less fabulous than others — the states, that is, not the plays!). Broom Street begins what will be four years of productions with a compilation of plays from the Midwest. Shows are at 8 p.m. Thursday-Saturday (no show Aug. 3); advance tickets at bstonline.org.

Rooftop Cinema, Aug. 10-31. Madison Museum of Contemporary Art: It’s back, for its 18th summer! MMoCA’s Rooftop Cinema series will fill State Street’s night sky with something other than the Orpheum sign as the museum screens art films for four Thursdays this month. The first is Inu-Oh, an anime feature film with a glam-rock sensibility and a social conscience, nominated for a Golden Globe in 2022. Subsequent Thursday films are Alma's Rainbow, Earth II and Rewind & Play. Bring your own chair or blanket; water and snacks will be sold on-site (no carry-ins). Films begin about 20 minutes after sunset and it’s recommended attendees find their seats by 8:10 p.m. More info at mmoca.org.

Find the individual Picks collected here, and as part of the full calendar of events.