From Bad to Worse/Newspaper Comics


 * FoxTrot had an arc where Roger, after a horrible business trip (which could be an entry in itself) that ended quits him returning to his son needing stiches, quits his job. He then proceeds to find out that none of his family has time (or wants) to hang out with him. To gain money, he invests... in an infomercial, losing money. He then tries stock trading... and loses more money. After all of this, he ends up going back to his job, having lost a number of paychecks, a large amount of money, and his computer, and gaining a cut in pay at his job.
 * Peanuts:
 * Few of Charlie Brown's failures were as bad as the time he tried to compete in the school spelling bee. Despite both Violet and Lucy warning him that he would "make a fool of yourself", he signs up, spends time preparing for it and studying grammar rules (though still confused about the "I before E" one) seem very confident he can handle it, but then misses in the first round. (The word he gets is "maze", and the first thing to come to his head is Willy Mays). The whole class laughs at him, and he gets an "I told you so" from Violet. But it gets worse. He's so upset that when his teacher asks him what's wrong, he yells at her ("Og good grief, now I've done it!") gets sent to the principal's office (which has never happened to him before), and while the principal lets him off easy, goes home bemoaning how it was truly the worst day of his life, and he can't even count on his faithful dog to greet him, as Snoopy is more concerned with pretending to be the World War I Flying Ace hunting the Red Baron.
 * A more lighthearted example; in one strip, Charlie Brown comes to the sandlot to find that Lucy has "borrowed" dirt from his pitcher's mound for her new plant. Then, four other members of the team do the same thing. Finally, he blows his top and demands they return it, shouting that "I want my pitchers mound to be just the way it was!" The mess he ends up with is not the way it was.