Before long, Bill had become an excellent guitar player and began jamming with bass player Jim Stillman and drummer Bob Korum. Bobby tried every angle imaginable to join the group sessions but Bill thought he was too young. "I kind of backed into the band. I used to make all kinds of deals with my brother to come along and practice. When he finally let me join him (if I would promise to keep quite) I was aware that they didn't know any of the songs lyrically and I just happened to know them all. I was fifteen years old and my ears were glued to the radio. It didn't take long before I started singing the songs and they started Rockin' along." Before long, Dick Dunkirk took Stillman's place on bass guitar and The Shadows became one of the top new bands in the area.
At this point, as the result of a tragic twist of fate, Bobby's story begins to take on a bitter sweet flavor. The date was February 3, 1959. A light plane carrying Buddy Holly, Richie Valens, The Big Bopper and 20 year old pilot Roger Peterson crashed in a snow covered Iowa field, killing everyone on board. Only minutes earlier they had finished their performance at the Surf Ballroom in Clearlake, Iowa and had rushed to the airport in nearby Mason City to catch the charter plane that was to bring them to their next engagement in Moorhead, Minnesota. News of the tragedy traveled fast. People at the local radio station in Moorhead, like everyone, were in a state of shock. The rest of the tour had arrived by bus from Clearlake after a cold and snowy all night drive. A decision was made to continue on with the show. The promoters asked for local talent to help fill in that sad night and as the curtain came up that evening, a new voice was introduced to the world. A fifteen year old voice that knew all the words to all the songs, Bobby Vee. In the following thirty plus years Bobby would go on to place thirty-eight songs in the Billboard Hot 100 chart, with six Gold singles, fourteen Top 40 hits and two Gold albums. But that night, instead of a seat in the audience, Bobby and his brother Bill along with The Shadows took the stage in memory of three of rock 'n' roll's brightest stars.
Their first paying gig was on Valentine's Day 1959. They drove 45 miles in zero degree weather in a heaterless '51 Oldsmobile to play on benches that had been pushed together to form a makeshift stage. In the middle of the show the benches pulled apart and the amps smashed to the floor. Not exactly the kind of impact they were looking for. The band made $60, which any musician can tell you was damn good for a first gig in those days. June 1st 1959, Bobby and the group went to Minneapolis, Minnesota to record a song for Soma Records that Bobby had written called "Susie Baby". By the end of the Summer, "Susie Baby" had reached number one on all the local stations in the upper mid-west and major record companies were calling with interest in signing this new young singer. Bobby Vee And The Shadows signed with Liberty Records in the Fall of 1959 and the band continued on until 1963, when Bill, deciding the road was not to his liking, left to pursue interests closer to home.
In late 1960, after a couple of songs had barely inched their way into the national charts, it appeared that Liberty was losing faith, when a radio station in Pittsburgh, PA began playing the back side of what might have been Bobby's last single. The song was "Devil or Angel". It had been an R&B hit a few years earlier by a group called The Clovers and was a favorite of Snuff Garrett, the young producer responsible for signing Bobby to Liberty. Following the record's success in Pittsburgh, "Devil or Angel" went on to reach the Top 10 in city after city. By the end of 1960, it peaked at number 6 on the Billboard Pop chart, as well as reaching the Top 20 on the R&B charts. Liberty Records exercised its option and signed Bobby to a five year contract.
If "Susie Baby" served as Bobby Vee's entrance into the world of Billboards Hot 100, then "Devil or Angel" was certainly the foundation for a string of hit records reaching the nations Top 20 throughout the entire '60s era. Bobby followed with "Rubber Ball" (#6) later in 1960. One year later his biggest hit, "Take Good Care of My Baby" spent three weeks at number one, followed by the number two "Run to Him", and the Top 20 hits "Please Don't Ask About Barbara (#18), "Sharing You" (#15 and "Punish Her" (#20). Bobby's hits were not limited to America. By 1963 he had collected seven Top 10 hits in England as well as a number 2 album called "Bobby Vee Meets The Crickets" and in 1963 shared the charts for forty weeks side-by-side with The Beatles.
His fame appeared to wane after the Top Ten single "The Night Has a Thousand Eyes", due in large part to the success of The Beatles and other English acts. Vee appeared in several movies, including Just for Fun and Play It Cool. He briefly tried to cash in on the British phenomenon with the disappointing "Bobby Vee Sings the New Sound from England!" and also recorded songs by his early influences, including Buddy Holly And The Crickets. Bobby Vee continued to chart throughout the 1960s, and even hit the Top Ten again in 1967 with "Come Back When You Grow Up", but after a brief attempt at more serious recordings, and flower power music taking over the charts, Bobby hit the Rock 'n' Roll oldies circuit. His tours took him to Japan, Australia and Europe as well as the United Kingdom. His recording career produced over twenty-five albums including a Gold Album from England for his 1981 "Singles" L.P. Back in the U.S., Billboard magazine called him, "One of the top ten most consistent chart makers ever."
Into the 1990s, with the continuing demand for product by Classic oriented radio stations and collectors alike, EMI/Cema issued a twenty-five song re-mastered compact disc and cassette as part of the Legendary Masters series. Late in the year, a re-issue of his 1963 Christmas album was made available. To coincide with his sold out 1990 tour of England, Bobby issued a seventeen song collectors edition cassette called "U.K. Tour '90" on his own Rockhouse Record label. The tape, an anthology of sorts, included new material recorded with his sons, as well as several previously unreleased songs from past years. In 1994, critics and collectors gave great reviews to his "Last Of The Great Rhythm Guitar Players" CD. As testimony to Bobby's high energy show and continued popularity, the annual readers poll by sixties music magazine The Beat Goes On voted him: 1991 Best American Act; 1992 Best Live Performer; 1993 Favorite Male Singer; and in 1994 he was named runner up to Paul McCartney in the category of Most Accomplished Performer.
On June 20, 1999, Bobby was presented The Theodore Roosevelt Rough Rider Award by North Dakota's Governor Ed Schafer. The Rough Rider Award is the highest recognition given by the state to native North Dakotans. Gov. Schafer said, "Throughout his success, Bobby has maintained his North Dakota roots and values. He is praised by many of his peers not only for being a talented performer, but a kind, good and humble person. I am extremely proud to honor him with this award."
Between Europe and America, Bobby and his band performed about a hundred dates a year. When he was not touring or working on his own music, he was involved in the production of various other musical projects at his Rockhouse Recording Studio, located outside of St. Cloud, MN.
In October 2007, he was still on tour, performing in The Last of the Big Rock Shows along with Lesley Gore and Billy "Crash" Craddock in Australia. In the Fall of 2011 he was in the recording studio working on a new album and writing new songs. Sadly, in May of 2012, 69-year-old Bobby announced that he had been diagnosed with Alzheimer's disease. "Needless to say it was a moment that stunned my family and myself to the core," he posted on his website. "Since this time I have chosen to remain private and to focus on what is most important to me: my family and my music." Sadly, Bobby passed away on October 24th, 2016, at the age of 73.
Bobby Vee once kicked Robert Zimmerman out of his band because he thought he had no future as a musician. Zimmerman would go on to have a career as a folksinger, calling himself Bob Dylan.
For more, be sure to read Gary James' Interview With Bobby Vee