A demonstration disc, recorded with the artist's high school group the Delphis, alerted Kapp Records to Hyland's vocal talent. In 1960 he enjoyed a US chart-topper with 'Itsy Bitsy Teenie Weenie Yellow Polkadot Bikini', one of the era's best-known 'novelty' recordings which subsequently sold over one million copies. Having switched outlets to the larger ABC-Paramount Records, the singer enjoyed further success with 'Let Me Belong To You (1961 - a US Top 20 hit) 'Ginny Come Lately' (1962 - a UK Top 10 hit), before securing a second gold award for 'Sealed With a Kiss'. Its theme of temporary parting was empathetic to the plight of many love struck teenagers and the song returned to the UK Top 10 in 1975 before being revived in 1990 by Jason Donovan. Hyland continued to enjoy US chart entries, notably with 'The Joker Went Wild' and 'Run, Run, Look And See' (both 1966), but reasserted his career in 1970 with a sympathetic version of the Impressions' 'Gypsy Woman'. This third million-seller was produced by long-time friend Del Shannon, who co-wrote several tracks on the attendant album, but this rekindled success proved short-lived and the artist later ceased recording.