Little Orphan Annie - The last creative team to work on Annie did the best they could to update this 86-year-old strip. Annie started wearing jeans, the stories had contemporary settings, but it was all for naught. People who came to the comic because they loved the movie didn't relate to the adventure-style stories. Unlike times past, readers are receptive to new gag strips, but are completely uninterested in new (or even revamped) narrative strips. A noble effort, nonetheless.
Gasoline Alley - This is one of the few strips where characters age (albeit not quite as quickly as in the real world). The current artist, Jim Scancarelli has made major changes in Gasoline Alley, keeping the story -- and the world it inhabits -- growing and evolving. Phyllis Wallet, a mainstay of the strip since the 1930's died of old age during his tenure. Characters leave the strip, and new ones appear. Situations change, and children are born. Just like the real world, life goes on. Slow, organic growth that results in major changes over time.Very fresh, though with a patina of age.
Prince Valiant - Another strip where characters age. When Hal Foster created Val, he was a young boy newly arrived at King Arthur's court. Over a half century later (being a Sunday-only strip, time moves very slowly), he's now a late middle-aged family man. The current creative team of Gary Gianni and Mark Schultz are moving the stories in a more fantasy-oriented direction, bringing them in line with current tastes of comics readers. Maintaining the high standards of the past in contemporary form, fresh in look and stories.
Brenda Starr - Currently written by a journalist, this strip has dramatically changed since Dale Messick's death. Characters have aged, and the trials and tribulations of Ms. Starr reflect the current unsettled market of newspaper reporters in general. The strip has hit the right balance of adventure, drama, and commentary on the very medium it's printed on (thanks to current writer Mary Schmich, a reporter for the Chicago Tribune) and a clean, modern graphic look as drawn by June Brigman. Building a new story on a strong foundation -- fresher than the newspapers that carry it.