Can annual plants live more than one year in controlled environments or in the wild, and if so, what's the oldest living annual?

Yes they can. An annual is a plant that completes its life cycle within a year.
There are some that whilst classed as an annual can take two years or sometimes more to complete the life cycle. They then produce seed and die.
I guess in a controlled environment if one could prevent or delay the cycle of reproduction then an annual could be maintained for longer.
I have no notion as to the oldest annual plant.

Certain annual plants in the UK are killed off after the first frosts. If they are protected from frost and moved indoors and regularly dead headed and pruned to keep them so that the roots can maintain the growing cycle, they can be kept for more than their normal life span.

Almost any plant can go to seed and grow again the next year. Many varieties of Petunia, if allowed to go to seed, will grow as 'volunteers' the following season. ('Volunteer' is the term for an annual which has grown again the following year.) However, almost always any hybrid properties are lost in this next generation, leaving a small, single petaled pale purple blossom, instead of anything fancy.

Tomatoes, usually considered 'annuals', will also come up as 'volunteers'. However, usually 'volunteer' tomatoes will not bear fruit, or if they do, they bear too late in the season to ripen.

It is worth remembering that the only plants which will not voluntarily grow again the following year without replanting are plants which have been engineered by humans. Hybrids, grafts, etc. Plants which did not occur naturally. The natural or native cousins of these altered plants will continue to flower year after year. Its just the way plants work. If a plant couldn't reproduce, it wouldn't still be here.