Like a number of singer-songwriters, Cheryl Wheeler is known for her deep poetic musings on life, relationships, and politics. She can write a touching song like “75 Septembers,” drawn from her father’s life, or pen an anti-gun message in a song like “If It Were up to Me.” “She has a wide streak of tenderness,” noted the Toronto Star, “but reveals herself as a mature artist unafraid to sing about what she thinks and feels.”
Wheeler, however, also enjoys writing humorous songs, and at least one writer has suggested that if she had not become a singer, she probably would have been a stand-up comic. Songs like “Is It Peace or Is It Prozac” seem to provide balance, a short break from relationship woes and the problems of the world. “Straddling the line between folk and country,” noted David Okamoto in MusicHound Folk, “Cheryl Wheeler’s biggest challenge has been squeezing both of her music personalities - sensitive songwriter with sinister satirist - onto one album.” Her ability to balance pathos with satire has also made her extremely popular on the coffeehouse circuit. “If singer/songwriters were immortalized like presidents are on Mount Rushmore,” wrote Gordon Ely in the Richmond-Times Dispatch, “the first face carved would have to be that of Cheryl Wheeler.”
Wheeler was born on July 10, 1951, in Timonium, Maryland. By the age of ten she was interested in music, playing first the ukulele and then the guitar. She took lessons from a neighbor, and together they practiced every song they knew for hours on end. Wheeler performed publicly for the first time at a Hootenanny show when she was twelve; by the time she was 17, she was writing her own songs.
Wheeler began performing professionally in the Baltimore, Maryland/Washington, D.C. area, where one of her first gigs was at a Steak and Ale restaurant. She later recalled that the restaurant only had one public-address (PA) system, which meant that her songs were sometimes interrupted by “Smith, party of five ... Smith, party of five.” Eventually she convinced the management to buy a second PA system. In 1976 Wheeler moved to New England, where she continues to reside. She recorded a 1983 EP called Newport Songs with the help of country-folk singer-songwriter Jonathan Edwards, followed by Cheryl Wheeler in 1986, and the promotional tape, Live and Otherwise, in 1987, both released on the North Star label.
In 1990 Wheeler got her big break when Capitol’s Nashville division signed her. Randy Travis, noted for his production work, added polish and country-style arrangements to Circles and Arrows, but the album failed to find a niche on country radio stations. “They just did not know what to do with me,” Wheeler told the Austin American-Statesman. Although her stay in Nashville was brief, Wheeler remained unfazed by her lack of commercial success. “I do not want to ride around the country in a bus,” she told Judy Monchuk in the Kitchener-Waterloo Record. “I do not want to be in a band. I don’t want to be looking at the fast lane and not paying attention to the lane I’m in.”
In the early 1990s Wheeler found a more permanent home for her music at Philo Records. She also hit her musical stride with the release of Driving Home in 1993. Richard Meyer noted approvingly in All Music Guide that the production, vocals, and songwriting surpassed her earlier efforts. Wheeler followed her Philo debut with Mrs. Pinocci’s Guitar in 1995 and Sylvia Hotel in 1999. “Personal relationships have been the grist of songwriters for hundreds of years, and these days, for hundreds of songwriters,” noted George Graham of Sylvia Hotel on WVIA-FM radio in Pennsylvania. “Cheryl Wheeler breathes new life into familiar subjects and creates an excellent album that you’ll want to keep going back to.”
Wheeler unintentionally courted controversy in 1998 when she released “If It Were Up to Me,” a song inspired by a school shooting in Jonesboro, Arkansas. The song ends with “If it were up to me, I’d take away the guns.” Political conservatives condemned the song’s anti-gun lyrics; liberals praised its gun-control message. “If we could understand why people become violent, that would be great,” Wheeler told Scott Alarik in the Boston Globe. “But all we know is that the reason these people are dead is that they had bullets go through their bodies.” Rounder Records responded to the controversy by pledging to donate five dollars to the Center to Prevent Handgun Violence every time the song was played on the radio.
Of her compilation album, released in 2001, Wheeler told Cathalena E. Burch in the Arizona Daily Star that it wasn’t a greatest hits collection: “I’ve never had any hits.” Her songs, however, have been placed on the charts a number of times by other singers. Dan Seals reached number one with “Addicted” and Suzy Bogguss took “Aces” to the top ten. Wheeler’s songs have also been recorded by Bette Midler, Maura O’ Connell, and Juice Newton. The fact that other artists often choose to record her songs also is due in large part to her meticulous writing style. “I think more about songs than albums,” she told the Austin American-Statesman.
Wheeler travels constantly, spending as many as 150 days per year on the road, and has developed a reputation as an inspired live performer. “Wheeler’s shows mix her achingly poignant ballads with moments of hilarious levity,” wrote Burch. While her busy road schedule helped bring an end to her marriage, she admits to enjoying life on the road. “Doing a live show, for me,” she told Andy Smith in the Knight-Ridder/Tribune News Service, “is very different from making a record. When you do a record everything becomes a big deal. I’d much rather just go out and play for people.” As far as fame, fortune, and the future goes, Wheeler seems content with the life she’s chosen. “I never think ahead,” she told Ely. “I think I am going to have a tuna fish sandwich for dinner tonight. At the moment, I fully intend to go to the store for celery and a can of tuna. But that plan could change at any moment.”