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Rihanna will play the Air Canada Centre.

Moe Doiron/The Globe and Mail

Navigating Canadian Music Week can be a challenging venture, what with its sub-festivals and various ticket plans and passes. Conferences, award shows and speaking engagements abound, but the non-industry types will be attracted to the six-day affair for its Film Fest, Comedy Fest and Canadian Music Fest (which covers small-club showcase sets and loosely affiliated major gigs). Here are eight highlights.

Rihanna

At times it seems her relationship with her plus-one (Chris Brown) overshadows her number-ones (a dozen chart-topping singles). The midriff-baring Barbadian, whose musical decisions are sound, plays the Air Canada Centre for two nights, with CMW VIP passes gaining admittance to the second concert only. March 19, 7:30 p.m. $35 to $165. Air Canada Centre.

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The Jessica Stuart Few

The playful jazz-pop threesome celebrates its sophomore album, Two Sides to Every Story, an endlessly charismatic disc that includes a koto-speckled take on the Eurythmics' Here Comes the Rain Again. March 19, 9 p.m. $10 or wristband/pass. Courthouse.

Raekwon

Was he a member of the Wu faction, or was it the Tang division? The rap icon Raekwon, a member of the pioneering hip-hop family the Wu-Tang Clan, keeps busy with that group's 20th anniversary plans as well as a solo album (F.I.L.A.) due this summer. March 20, 9 p.m. $25 or limited wristband/passes. Sound Academy.

Outlaws & Gunslingers

Queen West cowboys and cowgirls gather for a night of literate song-craft and Americana melodies. Performers include gentle Justin Rutledge, classic-country throwback Daniel Romano, indie-folk songstress Oh Susanna and Blue Rodeo's crooning Jim Cuddy. March 20, 9 p.m. $15 or limited wristband/passes. Horseshoe Tavern.

Ain't In It For My Health: A Film About Levon Helm

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Described by director Jacob Hatley as a "hang-out film" or a "character study," this untraditional biopic on the Band's late singing drummer has more weed-related scenes than any music documentary outside the new one on Snoop Lion's smoke-filled reggae adventure. March 21, 7 p.m. $10 or wristband/passes. TIFF Bell Lightbox.

Funny As Hell Live

With misdirectional jokes and a laid-back edginess, Montreal comic Jon Dore has found a niche as the host of HBO Canada's Funny as Hell, a stand-up series that is presented live at CMW this week. March 21, 7:30 and 10 p.m. $35.20 or wristband/passes. Randolph Theatre.

Lee Harvey Osmond

Tom Wilson's freak-folk project is showcased with an enviable roster of special guests, including Cowboy Junkies' Margo Timmins, blues laureate Paul Reddick, the Skydiggers' Andy Maize and Colin Linden, who works with Wilson as part of the folk-rock trio-extraordinaire Blackie and the Rodeo Kings. March 22, 8 p.m. $39.50 or wristband/passes. The Great Hall.

Sandra Bernhard

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At age 57, the onetime one-woman bonfire has mellowed perhaps. What she may have slightly lost in edge, however, the unique cabaretist has gained in seasoning and charismatic style. March 22, 9 p.m. $39.50 to $49.50. Winter Garden Theatre.

Canadian Music Week, March 19 to 24. $10 for most showcases and $60 for a six-day wristband ($120 for a VIP pass). CMW.net

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