(July 21, 1949)
One of the earliest strips, and Wilson's already ingeniously subverting the basic premise, having the obligatory last line (which is also the strip's title) being distorted by to the mischeivous (and, uncharacteristically, whiskered!) Cat-Cat.

(December 30, 1952)
As a generation of soldiers put down their weapons and settled into Suburbia, they face a whole new set of problems--among them the challenges of marriage and child-rearing.
Wilson mirrors such anxieties impeccably in his early 50s work; rather than just viewing Cat-Cat as a troublesome alter-ego, Colonel-Major Leakage assumes a quasi-parental role.
The December 30th comic seems to reflect Wilson's attitude toward corporal punishment.
Leakage thinks that Cat-Cat's (presumably) terrible ation warrants an equally terrible punishment, but this only flames Cat-Cat's rebellious tendencies further.
On a more superficial level, the Colonel-Major's use of his pet's 'full name' ("Cat-Cat the Cat") parodies a common parental habit.

Though Wilson had no children in 1952, his daughter Molly was born just over a year later, so it is not unreasonable to assume he had parenting on his mind.

Wilson had a lasting friendship with Flash Gordon creator Alex Raymond and critic Phil Ingels suggested that this strip might be a subtle criticism of Raymond's parenting technique ("Cat-Cat in the 50s", The Comics Critique, April 1994), though I think this is a bit of a stretch.

(September 3rd, 1957)
This one isn't very historically notable, I just think it's funny.

(November 14th, 1962)

After seeing an enticing rise in syndication numbers, Brian Greene, Wilson's editor at the Associated Syndicate, asked Wilson to revamp the strip for a full color Sunday format. Wilson refused, on the grounds that an increased number of panels would interfere with his rhythmic (some would say "formulaic") humor style.
As a concession to Associated, Wilson agreed to have the daily strip colored, and the strip was relaunched as "Cat-Cat Adventures" on July 19, 1959, Cat-Cat's 10th anniversary.
While casual readers were mostly indifferent, fan response was overwhelmingly negative. Many objected to the color choices for Cat-Cat and the Colonel-Major, even though the selections were largely Wilson's.
Many paper's daily comics pages were black and white anyway, so even comparitively attractive strips came across as simply muddled.
AFter a few years of Cat-Cat in color, Greene admitted his error and allowed Wilson to return to his classic zip-tone shading.
In 1963, cat-Cat reverted to its classic look, as it would remain for the rest of Wilson's run.

This particular strip was one of Wilson's favorite of the color years. "The last panel would've been all but impossibly in black and white," Wilson told The Comics Journal in 1987, "The coloring brings out the sheer oddity of Leakage's dinner guests."
"I hope Jack there likes pancakes!" he added, referring to the strip's bizarre caricature of John F. Kennedy, dressed in an "Uncle Sam" costume and covered in pancakes.
Caricature was seldome seen in Wilson's cartooning, and it's hard to say why he chose to include the then-president here.

(May 7, 1966)

The choice of setting for the "mislead" second panel is interesting; though Cat-Cat did not go to Thailand after all, Wilson in fact did, spending a year and a half living with his wife and young children in a crowded flat in Chiang Mai.
When I met him at Comic-Con in San Diego, Wilson's son Christopher told me that the move to Thailand was one of his father's "stranger inclinations," though he said he'd like to move back when he can afford it.
The move to Southeast asia no doubt gave Wilson a different view of U.S. foreign policty--for the first time since the strip's inception, Leakage loses the USAF on his shirt pocket and during this period he was seldom referred to by rank.
Whether this was a deliberate political statement or merely an attempt to keep the strip from seeming dated is uncertain.

(December 8, 1966)

After some time in Thailand, the agin Wilson's output began to notably decrease and in late 1966 Associated had Wilson's longtime New York assistant, Hugh Crocker, take over the brunt of the strip, with Wilson's role reduced to "creator and contributing artist."
This strip is typical of Crocker's Cat-Cat. The feline has taken on a more sinister edge--evolving from a screwball child to a rebellious (even criminal) teen.
It is believe that the first panel was Wilson's, while Crocker was responsible for the rest. however, Wilson's criticism of Crocker's more anthropomorphic cat does make it into the strip, as the narrative caption about Cat-Cat's lack of thumbs.
When Wilson returned to the States, he resumed a more active role, but the presence of Crocker and other artists is evident in all subsequent strips.
Some fans contend this is why Cat-Cat the Cat fizzled out less than a decade later, but I'm more inclined to think that the strip was too naive to seem cutting-edge in a post-Watergate world, while lacking the kind of middle-American cuteness that kept strips like Peanuts well-loved.