Cheryl Wheeler has to be seen to be appreciated. Nothing you read and nothing you hear from her albums prepares you for how good a performer she is.
You may not be familiar with Cheryl, but you have probably heard her music. She is very respected as a songwriter by her peers, which can be seen by how many of them record her songs. Chery's songs have been covered by artists as diverse as Dan Seals, Peter Paul and Mary, Kenny Loggins, Garth Brooks, Suzy Boggus, Melanie, Bette Midler, Maura O'Connell, Sylvia, Kathy Mattea, and Holly Near. If they think she is great, then you owe it to yourself to learn more if you aren't familiar with her.
From her albums you can tell that she is a gifted songwriter with a beautiful voice. From other people's comments about her you can learn that she is a natural story teller with a fantastic sense of humor. But until you see her in person, you never really believe what you've been told about her. Besides, almost half of the songs she does during her shows haven't been recorded!
If you have never seen her do a live concert, then by all means do so! I get e-mail from people all the time thanking me for spreading the word about Cheryl. They go to the concert knowing they will enjoy it, and often find it even better than they had thought it would be. If she doesn't ever perform near you, then try to find a copy of her video or her live album. and see what you are missing. You can find some clips of her on YouTube, but they are usually only the songs, and not the stories. If she ever performs near you, do what you can to attend. If you don't, you will kick yourself later for missing a great show.
Her Career
Cheryl's first concert was to a captive audience. She found an old toy ukulele in a neighbor's attic and serenaded her mother who was taking a bath at the time. A year later she got a real ukulele, then finally got her first guitar. She learned guitar from a neighbor, who also taught a group of boys. Each week they would get together and play just about any song they could think of for hours on end. Her first public performance was at a Hootenany type show when she was 12. She started writing songs when she was 17.
She has never had a "Day Job". Her first professional gigs were at the Steak and Ale Restaurant in her home town of Timonium, Maryland. The place only had one PA system; in the middle of her songs you would hear: "Jones, party of four ... Jones, party of four". She finally convinced them to get a second PA system. 
Cheryl did have a "job", teaching music. In her words:
I did have a job for a few years, "teaching" music at Jemicy School, a wonderful school in the Baltimore area for kids with dyslexia. ("Teaching" is in quotes so as not to suggest I had the training or skills of an actual teacher). I was filling in for the music teacher who had left, and after a few days, I told the director she needn't be in a hurry to find an actual teacher. I just played guitar and sang with the kids. We put on shows, both at the school and at a local library and a nursing home. Those kids were brilliant. I loved it. During that time I was also doing local bar gigs at night and after a few years I felt like I wanted to devote all of my time to playing and writing, so I moved up here to New England and did that.
She performed at venues around Baltimore and Washington DC before moving to New England in 1976, where she now lives. She tours extensively. She had a band for a while, but usually performs solo now, or with Kenny White, who often opens and then accompanies her and sings backup. She often appeared in the On a Winter's Night tour, and was part of the Philo 25th Anniversary tour.
Her Albums
In 1983, Cheryl released a self produced EP called Newport Songs. Her first two albums Cheryl Wheeler in 1986, and Half a Book in 1991 were on an independent label, North Star. That company also released a promo tape called Live and Otherwise in 1987. This was a bonus tape that was sent to anyone who filled out a survey form that was included in a number of the North Star albums.
Her third album, Circles & Arrows, was originally released on Capitol in 1991, but it was dropped almost immediately due to a political shakeup with the label company. (The people who had promoted her album were let go, and Capitol decided to heavily promote Garth Brooks)
Her fourth album Driving Home was on Philo in 1993, a division of Rounder, and produced three singles: Almost, Silver Lining, and 75 Septembers, a song written for her father, and covered by Peter, Paul & Mary on their album Life Lines.
Rounder later reissued Circles & Arrows in 1995, followed by Mrs. Pinocci's Guitar in 1995, Sylvia Hotel in 1999, the compilation album Different Stripe in 2003, and finally Defying Gravity in 2005.
In 2003, Cheryl graciously allowed the creation of No Previous Record, a two-disc album of songs that were never released on a commercial label. This album consisted of audience, FM, and soundboard recordings, and is restricted to members of her email list.
In 2009, Cheryl released Pointing at the Sun on her own label, Dias Music. This album includes some of the songs that appeared on No Previous Record, along with other new songs and a remake of Summerfly.
In 2012, Cheryl finally released a live album Cheryl Wheeler Live at the Triple Door, featuring Kenny White. If you have seen these two in concert, you know how great this album is. The album has the complete concert, including the stories and patter between songs. If she doesn't perform in your area very often, here is a great chance to enjoy one of her shows.
In 1998 a video of a live concert was released, What Do I Care? I Don't Have Any Kids Construction Company. The film had been shot a few years before, so that by the time it came out, Cheryl's act had changed enough that people who saw the video would still see a different show when they went to see Cheryl perform. Unfortunately, this video is out of print, although there are reports of used versions appearing on amazon.com and eBay.
Her Songs
Cheryl's songs are often emotional portraits of people, leaving you with the impression that you know the characters. You find yourself being dragged into the song rather than standing outside and observing. Other songs by Cheryl are hilarious situation comedies.
From her songs you can get glimpses about her childhood: She was a Tom-Boy ( I Know This Town ) who loved music ( Music In My Room ).
You can also get glimpses of her adulthood: Her move to New England ( Northern Girl ), her neighbors ( Quarter Moon and His Home Town ), her surroundings ( When Fall Comes to New England, and The Storm ), and her time on the road ( Rainy Road Into Atlanta, Lighting Up the Mighty Mississippi, and Sylvia Hotel ).
But the songs that touch people the most are her songs about relationships, such as Arrow, Aces, and But the Days and Nights Are Long (formerly "Boulder Hotel Room"), and Gandhi/Buddha.
Cheryl's funny songs are legendary. Unfortunately, the early ones were almost never recorded. One notable exception was Estate Sale for which a video was made. Cheryl has always said that doing a funny song live is quite different than recording one. I guess enough of us have complained, because starting with Mrs. Pinocci's Guitar funny songs started appearing on the albums. For some reason, Cheryl's funny songs stay funny. I know of other artists who do funny songs, but after a few listens, I grow tired of them. During a show, I find myself laughing at jokes I've heard many times before. She is a natural story teller and a gifted comedienne, so each telling is fresh and often slightly different.
Her Concerts
If your idea of a folk singer/songwriter concert is a bunch of people clapping politely after songs, and then sitting quietly while the performer says things like "This next song is about ...", well, you've never seen a Cheryl Wheeler concert before.
Cheryl's concerts are more like what you would find at a comedy club than expect to find at a folk music concert. She will tell a story that has you rolling in the aisles, and then sing a song that leaves you wiping tears from your eyes. She will talk about some serious current event, and then sing a song that will have you howling with laughter. Her entire concert is an emotional roller coaster.
Her set list is usually a crumpled piece of paper with a bunch of song titles. After each song, she'll look at the list and decide what to do next. If somebody calls out a request, and her guitar is in the right key, she might try it, even if she hasn't done it in a while. If she just finished writing a song, she will usually try it out in front of the next audience. If she has two sets back to back, she almost never does the same (or even similar) group of songs.
Her funny stories between songs show as much diversity. Each time she tells a story, it will be a little bit different, so even if you've heard it before, you still find yourself laughing.
To repeat, there is no way you can read about Cheryl and get a good picture of what she or her concerts are like. You have to see one. If she is performing in your area, do whatever it takes to get to her concert. You won't be sorry.