HMAS Lolita (14) was formerly a luxury motor cruiser, commissioned as a channel patrol boat into and operated by the Royal Australian Navy (RAN) during World War II. She was one of thirteen similar vessels, known to Sydney siders as the 'Hollywood Fleet'.
She was built by W L Holmes of Neutral Bay and was launched in 1936 as Lolita II for Arthur Douglas Walker, a businessman and former Mayor of Mosman. When Walker sold his first Lolita (renamed Urallia), Lolita II became Lolita. By March 1940, Lolita was owned by H C Small, the proprietor of Small's Chocolates.
She was requisitioned and taken over by the Navy on 26 September 1941, commissioned by the RAN on 22 November 1941 under the command of Commissioned Warrant Officer Herbert S Anderson RANR(S). Lolita was returned to W L Homes shipyard for a naval refit - gone were the luxuries, painted navy grey and armed with .303 Vickers machine guns fore and aft and depth charge racks on the stern. She was finally purchased from Small on 18 May 1942, ten days after the Battle of the Coral Sea for 3,000 pounds. Following her requisition, HMAS Lolita carried out patrol duties at Port Kembla, Newcastle, Broken Bay and Sydney.
During the Battle of Sydney Harbour (often referred to as the attack on Sydney Harbour) by the Imperial Japanese Navy on 31 May and 1 June 1942, Anderson in command of HMAS Lolita then at the eastern end of the boom net, was called by the commander of HMAS Yarroma at the western end of the boom net, to investigate an object inside the western end of the anti-submarine boom net. Having identified the object to be an enemy submarine, Anderson notified the Port War Signal Station that he had sighted the submarine and was attacking. Given the submarine was located between the boom net and the Western Pile Light, Anderson was unable to make a passing run to drop Lolita's depth charges. He therefore motored Lolita stern first to the submarine where he rolled a depth charge off the stern and sped away to avoid the explosion. However, there was no explosion. Realising the water was too shallow, members of the crew attached floats to the second depth charge to slow its rate of descent so as to trigger the fuse. Having done so, Anderson again manoeuvred Lolita stern first to the submarine and rolled the second depth charge into the water. Again there was no explosion. As they approached to drop the third depth charge, the submarine exploded showering debris over Lolita and picking her up on the wave from the explosion. Subsequent investigations confirmed the crew of the submarine had triggered a self-destruct charge which severed the bow of the submarine killing both crew members. Members of Lolita's crew were satisfied that as they approached to drop the third depth charge, the crew of the submarine knew they had been spotted and as the 'game was up', they destroyed their submarine in an attempt to also destroy Lolita. Following the destruction of the submarine, Lolita resumed patrols.