Autumn arrives this week in the astronomical sense: The sun drops south of the celestial equator and stays there for the next six months.

Autumn arrives on the arts and entertainment calendar with multiple-award-winning acts.

First up is nine-time Grammy Award-winning singer Sheryl Crow, who’s performing at the Cumberland County Civic Center on Friday.

Second is singing sensation Liza Minnelli, one of the very few people to win a Grammy, a Tony, an Oscar and an Emmy. She’s opening Portland Ovations’ 2010-2011 season with a Sept. 29 performance at Merrill Auditorium.

Plus there’s six-time Tony Award-winning “Chicago,” a big Broadway show that’s wrapping up the 2010 summer season at Ogunquit Playhouse.

And Out & About resumes this week after a ‘tween-seasons hiatus. This column is now in its 19th year of highlighting the best in music and theater in southern Maine.

Sheryl Crow

Here’s something to crow about. One of the most decorated singer-songwriters of our time plays the Cumberland County Civic Center this Friday. We’re talking about Sheryl Crow, who has won nine Grammy Awards and sold nearly 40 million records.

Part of her artistic appeal and marketing power is that Crow covers a lot of musical territory, venturing into the subgenres of pop, rock, folk and country. In addition to vocals, she also plays guitar, bass and piano.

Many of Crow’s best efforts involve collaboration. For example, one of my favorite songs of recent years is the powerfully emotional “Picture,” an artistic foray into country with Kid Rock. Other collaborators include Michael Jackson and Don Henley; in the early days of her career Crow was a backup singer for both stars.

Another Crow hit that’s a personal favorite of mine is “Soak Up the Sun,” a solo pop tune with a very clever lyric; the song stays in your head a long, long time.

I expect that Crow’s Portland show, slated for 8 p.m., will include many selections from her most recent album (her seventh). It’s titled “100 Miles from Memphis” and ventures into the realm of soul. It came out two months ago with very strong early sales. Crow’s special guest in Portland is Brandi Carlile. Call the CCCC at 775-3458 or Ticketmaster at 800-745-3000.

Liza Minnelli

Portland Ovations – the new name for the organization formerly known as PCA Great Performances and prior to that, Portland Concert Association – opens its 2010-2011 season with a singer who was the youngest woman to win a Tony Award for Best Leading Actress. Liza Minnelli won her first big show business prize at age 19 in 1965 for her role in the Broadway hit “Flora the Red Menace.”

Ironically, “Flora” marked the debut effort by the Broadway creative team of John Kander and Fred Ebb, who would later write most of Minnelli’s signature tunes. Her best-known film role was sexy, sultry Sally Bowles in “Cabaret,” the hugely successful movie remake of the Kander-and-Ebb Broadway classic of the same name.

The famed composer-lyricist team thought so much of Minnelli that they wrote an entire television show for her: “Liza with a ‘Z’” aired in 1972 and marked the first of her many star turns on the little screen. Her signature tune is “New York, New York,” another Kander-and-Ebb effort.

When she picked up the 1973 Academy Award for her role in “Cabaret,” she completed a unique Oscar-winning family. Her parents, film director Vincente Minnelli and actress Judy Garland, had each won the award.

Minnelli’s recording career includes multiple studio albums, live recordings, singles and compilations. She can also be heard on numerous soundtracks of her Broadway shows and movies. Her 2002 album, titled “Liza’s Back!,” was released after her triumphant battle with encephalitis, a disease that threatened her ability to dance and sing. Her latest album, “Confessions,” is due for release the day before her Portland appearance.

Minnelli will be joined by her long-time musical collaborator, pianist Billy Stritch, who leads a sextet of musicians. The program includes a selection of American standards plus songs from her new album.

Portland Ovations presents Liza Minnelli in concert on Sept. 29 at 7:30 p.m. at Merrill Auditorium at Portland City Hall. Call PortTix at 842-0800.

‘Chicago’

“Chicago” is one of Broadway’s most decorated musicals, and this great show is getting a sensationally good Maine production this fall at Ogunquit Playhouse. And “Chicago” got its Tonys in a rather unusual fashion. All six of the statuettes are from the 1997 Broadway revival. The original production garnered numerous nominations but won none.

“Chicago” was originally conceived by dancer-choreographer-director Bob Fosse, who co-wrote the script, based on a 1926 play by Maurine Dallas Wilkins. The author of the source play was a Chicago Tribune reporter who covered several celebrity murder cases. Wilkins was distressed to see obviously guilty defendants walk free and voiced her disapproval of the justice system through her play.

For the score, Fosse brought composer John Kander and lyricist Fred Ebb – who had previously collaborated on “Flora the Red Menace” and “Cabaret” – into the project. Fosse stamped the show with his signature dance style that is characterized by angular poses emphasizing sexuality and cynicism.

The show is set in the 1920s and revolves around two women entertainers who murder their lovers and get away with it – thanks to the razzle-dazzle courtroom antics of a celebrity criminal lawyer.

Ogunquit’s fully professional (Equity contract) production stars Angie Schworer as Roxie Hart, who murders her lover on stage, and Rachelle Rak as Velma Kelly, who killed her husband before the curtain rises. Hart and Kelly meet in jail and form a vaudeville act.

Most of the action takes place in and around a Chicago jail, under the supervision of a corrupt matron of female prisoners. Other scenes take place in court, where George Dvorsky plays Billy Flynn, a lawyer with a penchant for show business and a deft ability to manipulate the press – portrayed as infinitely gullible.

I saw the opening night, and my top honors go to Schworer and Rak for their extremely athletic performances. “Chicago” is a high-energy show, and these two fine actresses project enough voltage to light up all of Ogunquit.

I also loved Dvorsky as the cynical lawyer and Sally Struthers as Matron “Mama” Morton, the equally cynical jail keeper. Another notable smaller role is performed by Paul Kreppel, playing Hart’s dim-witted husband.

Gerry McIntyre directs and he keeps the action at the frenetic pace it deserves.

Ogunquit Playhouse, a mile south of the village on Rt. 1, presents “Chicago” at various dates and times through Oct. 24. Call 646-5511 or visit www.ogunquitplayhouse.org.

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Liza Minnelli will open the 2010-2011 season for Portland Ovations on Sept. 29 at Merrill Auditorium.