| Billy had rushed to buy a banjo out after watching The Beverly Hillbillies.
He wanted to play bluegrass banjo, and he found one for £2 at the
Barras. He went to lessons at the folk centre in Montrose Street, but within
a short time, he had learned everything the teacher could teach him, so
Billy became the teacher for a while.
 Billy fell in
with the Folkie crowd, who were the wild hippie types of the time, with
long hair, drugs, and all the trappings of wild-child status. They went
around together all over the country, about thirty of them. Billy was not
an outstanding member at the time, and is remembered by the others as the
young, tall, shy welder. They frequented the Marland and the Scotia bars.
The Scotia still displays Billy memorabilia to this day.
During this time, Billy was in and out of various bands, eventually
forming The Skillet-Lickers with Jim Carey and George McGovern.
They played many gigs, some in England, until Billy dissolved to group
and soon joined The Acme Brush Company.
During 1965, Billy eventually settled on a two-piece combo The
Humblebums with ex-rock guitarist Tam Harvey. The group played
many gigs in Glasgow and became moderately famous. Billy was approached
by someone from the Transatlantic label, and was signed by them. After
a Paisley gig, Billy was approached by a young songwriter called Gerry
Rafferty, who wanted Billy to hear his songs. Although doubtful, Billy
agreed, and was surprised at how good they were. So Gerry Rafferty, who
in later years was to become famous with the band Stealers Wheel
and the classic song Baker Street, joined the Humblebums
to make it a trio.
The band gained fame, but Billy's jokes during the breaks between
songs was drawing as many people as the folk songs. Rafferty began to develop
his style, and this led to tension between him and Tam Harvey. Tam eventually
left the band, and the Connolly/Rafferty partnership went on to make two
successful LP records.
Billy was living the high life at this time - gigging around the
country, continually on the road, drink and all-night parties. The band
increased in size to a six-piece. Eventually the lifestyle took its toll
on him. Billy caught pleurisy and pneumonia.
But the band enjoyed great success, including a Royal Command
Performance, and were undoubtedly one of the most popular folk bands of
the time. But increasingly, Billy and Gerry Rafferty did not see eye-to-eye
on the content of the show. Billy's comedy began to take longer than the
songs, and Gerry often asked him to cut it out of the show. But Billy's
time with madcap outfits like The Acme Brush Company had made him unable
to be a grim serious musician. When Billy realized that the comedy was
his talent, and began to develop his stagecraft, a split seemed inevitable,
and The Humblebums eventually broke up in 1971
 During this
time, he met Irish Pressagh, who was an interior designer from Springburn.
Billy and Iris lived together for four years before getting married in
1969. Jamie, their first child, was born in December of that year.
When the Humblebums split, Billy decided to stay on in London,
and try to make it as a folk singer on his own, but failed. Eventually,
he returned to Glasgow, his wife and baby son, £500 in debt. Down,
but not out, Billy began to write letters to folk and comedy agents, offering
to play for just expenses. At first he was not successful, but eventually
he was offered a gig in Musselburgh - his first proper solo comedy gig,
and the success of these early shows led to later tours of the tough clubs
of northern England, where he developed his style further.
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