Tiger Lilly was a career criminal who briefly took up residence in Wood City. His face had a spotty complexion reminiscent of the flower that shared his name. He typically wore a beret, a short sleeved black shirt and smoked a cigar.
One of Lilly's illegal enterprises was producing sound effects for the local radio station. These sound effects of gruesome events (such as car accidents, dog fights, shooting victims, etc.) were considered shockingly realistic. Lilly produced them by causing the actual events.
Lilly was employed by Mr. Amard, a local drama critic and prominent citizen. After Lilly caused the wreck of a train, his activities were investigated by Dick Tracy, who was visiting from out of town. Tracy traced the wreck to Amard, who was prepared to implicate Lilly. Lilly had Amard abducted, and left him to die in an explosion Lilly arranged at an abandoned tavern. Lilly then disbanded his gang, destroyed his remaining recordings and planned to go into hiding.
Lilly went to the Tiger Rest Golf Club in a town called Haver. He was tracked there by the amputee nurse known as "Frizzletop". Frizzletop had known Tiger’s brother John when she had been serving as a military nurse in the Philippines. She was looking for Tiger to let him know that she had been engaged to marry John, but he had been killed in action. Tiger didn’t believe her at first, but when she showed him the ring John had given her, he recognized it as his mother’s. He then took a liking to Frizzletop and hired her to work in the clubhouse that he had taken over.
Tiger and his gang were working a scheme to trick investors into believing that there was a valuable sulfur spring on the property. Frizzletop suspected something was afoot, and allied herself with Tracy and Junior, who were on the premises posing as a groundskeeper and caddy respectively. Tiger had lured an investor named Harvey Chance to the course, and Chance was prepared to pay Tiger fifty-thousand dollars cash for what he believed was a restorative hot sulfur well. Tracy intercepted Chance before he completed the transaction and showed him the rig and pumps that Lilly had used to fake the sulfur spring.
Crossing Dick Tracy
At the same time, a member of Tiger’s gang had discovered Tracy’s real identity. He told Tiger, who became suspicious of Frizzletop and Junior as well. Tiger sealed Tracy and Chance in his underground hideout while carbon monoxide gas from the industrial lawnmower poured in through the ventilation system. Tiger then tied Frizzletop and Junior up and set them adrift on a rowboat that he had knocked a hole into. Lilly expected them to sink and drown.
Through luck and resourcefulness, all parties survived these traps. Tiger and some of his men had retreated to a nearby hunting cabin, where they unwittingly attracted the attention of a local game warden. Lilly shot the warden and tied him and his dog to the steering wheel of the warden’s car. He then pushed the car into a shallow pond, expecting them to drown.
Fleeing on the River
The warden was weak from blood loss, but his dog was alert. The rope Lilly had used had enough length to allow the dog to tread water, holding the warden’s head up by the collar. They survived long enough to be found by Tracy, while Tiger Lilly and two of his men tried to escape on a raft.
The raft was pulled into the intake channel for a dam, and Tiger Lilly and his men were stranded. One of them tried to swim for shore, but was seemingly sucked under by the current. He escaped the dam but was killed in a gunfight with Dick Tracy (September 20th, 1942). Lilly and his remaining henchman were apprehended with the help of Junior and Frizzletop, who were pleased to see them taken to jail.
The Return of Tiger Lilly
Years later, Tiger Lilly was shown to be out of prison and working with Pouch. Tiger killed the drug dealer Dollar Bill, who was operating in the same park in which Pouch sold balloons. This annoyed Pouch, as it attracted unwanted attention from the police and Dollar Bill's supplier. Lilly attempted to intimidate Dollar Bill and ultimately killed him by breaking his neck. This caused a rift between the two men, but they continued to work together.
Later, Tiger Lilly helped Pouch pursue Aquarius, another criminal who had inadvertently bought one of Pouch's balloons that had valuable information concealed inside it. Lilly sneaked into Aquarius' home at the Bedwell Commune in an attempt to recover the balloon, but he was discovered. Aquarius and his associates tortured Lilly, then locked him in a shed behind the building.
Lilly was eventually able to escape from the shed, but he was seen by police who were investigating the Commune. Lilly fled and came across a pickup truck that was occupied by B.O. Plenty and Gravel Gertie. Lilly attempted to steal the truck, but Plenty fought and subdued him. Lilly was taken to St. Hilarie's Hospital for treatment. There, he encountered Pouch and the two men fought.
- Frizzletop was able to track down Tiger Lilly using official records and documents from the Draft Board. This tends to indicate that "Tiger" was his real name, not an alias.
- Throughout the Tiger Lilly adventure, the word "sulfur" was spelt "sulphur". The former spelling is considered more correct.