At age 17, he released the band's first AM hit single record, with its side A, "Humpty Dumpty", and side B, "Homesick", on radio station KFRC, in 1966.
He later became a performing, recording member in the Steve Miller Band, in which he wrote, sang, and played his original song, "Good Morning", as well as other album tracks, which appeared on their 1970 album "STEVE MILLER BAND NUMBER 5", on Capitol Records. He also played and sang on Steve Miller's 1972 released Anthology album.
In 1975, Bobby got a solo artist record deal with the Warner Brothers Record Company, and they released his album entitled, "BONAROO", with his original songs, "Life's Sweet Song", "Dream On", Melody Maker", "Spirit of a Dead Man", "I See the Light" and "Let's Go Down to the River".
In 1977, he contributed a co-authored song titled, "My Own Space", with lyrics by Jason Cooper, to the Steve Miller "BOOK OF DREAMS" album.
In 1995, Bobby, as a record producer and music publisher of the band, "Frumious Bandersnatch", released "NUGGETS FROM THE GOLDEN STATE: THE BERKELEY EP's", on the Big Beat Records label.
In 1996, "Big Beat Records" released Frumious Bandersnatch's "A YOUNG MAN'S SONG", containing: Jack King's' "Hearts to Cry", Bobby Winkelman's "Chain Reaction", and "Misty Cloudy", with Jack King's, and George Tickner's "Cheshire".
Also in 1996, Bobby self produced & released his "BONAROO II" CD, which included his original songs: "Nobody Asked Me", "We Can Move", "Magic Spell", "When You Touch My Hand" (lyrics by Linda Wallimann), "Where Ships Come Sailing By", and a new version of "Spirit of A Dead". Man". The title track on the CD was called "Children of the Stars". That CD also contains "Old Glory",& "Be Here Now" with the piano & organ as performed by Nicki Hopkins of the Rolling Stones fame, for his magnificent keyboard work on their original song entitled "You Can't Always Get What You Want". Lastly, "Off Again On Again Love" according to the label,is actually another original song entitled, "Rainbows (The Phantom Messenger)".
In 2002, Bobby and Alec Palao produced a full-length re-issued LP album entitled "FRUMIOUS BANDERSNATCH: GOLDEN SONS OF LIBRA (THE STUDIO OUTTAKES)", which quickly became a collectors' item soon after it was released world-wide by Get Back Records.
Bobby's' song, "Humpty Dumpty", was re-released in 2007, on the, Big Beat Record label, on "YOU GOT YOURS!" East Bay Garage 1965-1967 CDWIKD 268.
Also in 2007, "Hearts to Cry", was re-released again, after it was initially first released by the band back in 1967, on their clear purple, transparent, 33 1/3, four-song, LP album published by R. P. Winkelman Tunes. The song was originally penned and lead-sung by the band's original drummer, Jack King, who grew up in the East Bay Area of the San Francisco bay area.
The song appeared again on, "LOVE IS THE SONG WE SING (San Francisco Nuggets)" on the 'Rhino Record label.
This slick package included a four-CD, 65 long song set, inside its full-sized, 64-page big book, beautifully photographed and illustrated, in full color, and chronicalling the 1965 through 1970, "flower Power" years of the San Francisco bay area music scene.